Size, zeta potential, IC50 for MDA-MB-231 and MiaPaca cell lines for parent and CD-templated nanoGUMBOS [17].
\r\n
\r\nCoverage included:
\r\n- Preparation NiO catalyst on FeCrAl Subtrate Using Various Technique at Higher Oxidation Process
\r\n- Electrochemical properties of carbon- supported metal nanoparticle prepared by electroplating methods
\r\n- Fabrication of InGaN-Based Vertical Light Emitting Diodes Using Electroplating
\r\n- Integration Of Electrografted Layers for the Metallization of Deep Through Silicon Vias
\r\n- Biomass adsorbent for removal of toxic metal ions from electroplating industry wastewater
\r\n- Resistant fungal biodiversity of electroplating effluent and their metal tolerance index
\r\n- Experimental design and response surface analysis as available tools for statistical modeling and optimization of electrodeposition processes",isbn:null,printIsbn:"978-953-51-0471-1",pdfIsbn:"978-953-51-4991-0",doi:"10.5772/1913",price:119,priceEur:129,priceUsd:155,slug:"electroplating",numberOfPages:178,isOpenForSubmission:!1,isInWos:1,hash:"18ec8cf0e50c5e8170a9d0b20af09b7f",bookSignature:"Darwin Sebayang and Sulaiman Bin Haji Hasan",publishedDate:"April 11th 2012",coverURL:"https://cdn.intechopen.com/books/images_new/1455.jpg",numberOfDownloads:21268,numberOfWosCitations:25,numberOfCrossrefCitations:10,numberOfDimensionsCitations:23,hasAltmetrics:0,numberOfTotalCitations:58,isAvailableForWebshopOrdering:!0,dateEndFirstStepPublish:"April 12th 2011",dateEndSecondStepPublish:"May 10th 2011",dateEndThirdStepPublish:"September 14th 2011",dateEndFourthStepPublish:"October 14th 2011",dateEndFifthStepPublish:"February 13th 2012",currentStepOfPublishingProcess:5,indexedIn:"1,2,3,4,5,6,7",editedByType:"Edited by",kuFlag:!1,editors:[{id:"92970",title:"Prof.",name:"Darwin",middleName:null,surname:"Sebayang",slug:"darwin-sebayang",fullName:"Darwin Sebayang",profilePictureURL:"https://mts.intechopen.com/storage/users/92970/images/3175_n.jpg",biography:"Dr Darwin Sebayang was graduated from Rheinisch Westfaelische \nTechnische Hochschule Aachen- Germany (RWTH Aachen- Germany) on Light Structure. He is a professor in Faculty of Mechanical and Manufacturing Engineering at the Universiti Tun Hussein Onn Malaysia. The research focuses on light structure, engineering design and advance material and since five years ago he has been active on development of catalytic converter and exploring the application of electroplating of nickel to FeCrAl for catalytic converter.",institutionString:null,position:null,outsideEditionCount:0,totalCites:0,totalAuthoredChapters:"1",totalChapterViews:"0",totalEditedBooks:"1",institution:{name:"Tun Hussein Onn University of Malaysia",institutionURL:null,country:{name:"Malaysia"}}}],equalEditorOne:null,equalEditorTwo:null,equalEditorThree:null,coeditorOne:{id:"121404",title:"Prof.",name:"Sulaiman",middleName:null,surname:"Hasan",slug:"sulaiman-hasan",fullName:"Sulaiman Hasan",profilePictureURL:"https://mts.intechopen.com/storage/users/121404/images/system/121404.jpg",biography:"Professor Dr Sulaiman Haji Hasan has been teaching Manufacturing Engineering since 1980. 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\r\n\tPolymers are a new age material with wide applications in every part of the universe. As the backbone of the polymer is mainly composed of carbon, hydrogen, and oxygen their disposal after use is a universal problem unless it is biodegradable. Degradation is the scission of polymer backbone by breaking of various bonds and formation of copolymers. The degradation rates can be controlled by various parameters. The degradation results in loss of material from bulk due to polymer erosion. Also, different types of degradation brings the change in polymer properties due to its surroundings during their application as particular polymer/its composites. There are advantages and disadvantages of degradation as polymer composites can be used as protective material against the harmful environment. On the other hand, effective methods can be searched for non-biodegradable polymers. A database can be formed whenever such materials have industrial applications.
",isbn:null,printIsbn:"979-953-307-X-X",pdfIsbn:null,doi:null,price:0,priceEur:0,priceUsd:0,slug:null,numberOfPages:0,isOpenForSubmission:!1,hash:"10a018a7b05cf7b0b60648e17f09e974",bookSignature:"Dr. Pratima Parashar Pandey",publishedDate:null,coverURL:"https://cdn.intechopen.com/books/images_new/9200.jpg",keywords:"Polymers, Mechanism, Decomposition, Protective Material, Permeation Resistance, Hydrogenation, Degradation, Double Bond, Chain Scisson, Penetration, Swelling, Pyrolysis",numberOfDownloads:null,numberOfWosCitations:0,numberOfCrossrefCitations:null,numberOfDimensionsCitations:null,numberOfTotalCitations:null,isAvailableForWebshopOrdering:!0,dateEndFirstStepPublish:"March 18th 2019",dateEndSecondStepPublish:"September 20th 2019",dateEndThirdStepPublish:"November 19th 2019",dateEndFourthStepPublish:"February 7th 2020",dateEndFifthStepPublish:"April 7th 2020",remainingDaysToSecondStep:"a year",secondStepPassed:!0,currentStepOfPublishingProcess:5,editedByType:null,kuFlag:!1,biosketch:null,coeditorOneBiosketch:null,coeditorTwoBiosketch:null,coeditorThreeBiosketch:null,coeditorFourBiosketch:null,coeditorFiveBiosketch:null,editors:[{id:"142089",title:"Dr.",name:"Pratima",middleName:null,surname:"Parashar Pandey",slug:"pratima-parashar-pandey",fullName:"Pratima Parashar Pandey",profilePictureURL:"https://mts.intechopen.com/storage/users/142089/images/system/142089.png",biography:"Dr. Pratima Parashar Pandey is an Academician and Scientist in the field of Materials Science and Nanotechnology since last twenty five years. Earlier, she was in the field of polymer blends for twenty years and has published about fourteen papers in cited journals. Since, last ten years, she is in the field of metal nano polymer composites and has eleven research papers in SCI journals. She has written two chapters one, ‘Silver particulate films on softened polymer composite’ in the book ‘Applications of Calorimetry in a Wide Context - Differential Scanning Calorimetry, Isothermal Titration Calorimetry and Microcalorimetry’ Other, ‘Nano Biomaterials in Antimicrobial Therapy’ in a book ‘Recent Biopolymers’ published both in InTechOpen Publication. 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Venkateswarlu",coverURL:"https://cdn.intechopen.com/books/images_new/371.jpg",editedByType:"Edited by",editors:[{id:"58592",title:"Dr.",name:"Arun",surname:"Shanker",slug:"arun-shanker",fullName:"Arun Shanker"}],productType:{id:"1",chapterContentType:"chapter",authoredCaption:"Edited by"}},{type:"book",id:"878",title:"Phytochemicals",subtitle:"A Global Perspective of Their Role in Nutrition and Health",isOpenForSubmission:!1,hash:"ec77671f63975ef2d16192897deb6835",slug:"phytochemicals-a-global-perspective-of-their-role-in-nutrition-and-health",bookSignature:"Venketeshwer Rao",coverURL:"https://cdn.intechopen.com/books/images_new/878.jpg",editedByType:"Edited by",editors:[{id:"82663",title:"Dr.",name:"Venketeshwer",surname:"Rao",slug:"venketeshwer-rao",fullName:"Venketeshwer Rao"}],productType:{id:"1",chapterContentType:"chapter",authoredCaption:"Edited by"}},{type:"book",id:"4816",title:"Face Recognition",subtitle:null,isOpenForSubmission:!1,hash:"146063b5359146b7718ea86bad47c8eb",slug:"face_recognition",bookSignature:"Kresimir Delac and Mislav Grgic",coverURL:"https://cdn.intechopen.com/books/images_new/4816.jpg",editedByType:"Edited by",editors:[{id:"528",title:"Dr.",name:"Kresimir",surname:"Delac",slug:"kresimir-delac",fullName:"Kresimir Delac"}],productType:{id:"1",chapterContentType:"chapter",authoredCaption:"Edited by"}}]},chapter:{item:{type:"chapter",id:"69529",title:"Computational Analysis of Nanostructures for Li-Ion Batteries",doi:"10.5772/intechopen.88712",slug:"computational-analysis-of-nanostructures-for-li-ion-batteries",body:'We live in a world where most of the daily tasks in our life are dependent on energy like transport and communication over large distances. To satisfy the need for energy we have various sources, some of which are wind energy, solar energy, fossil fuel, nuclear energy, and so much more. For all of these, storage of energy in a device is an important part for which we have several kinds depending on the usage and need. Examples include capacitors, supercapacitors, batteries, fuel cells, flywheel, etc. A battery consists of one or more electrochemical cells and is connected externally to provide power to different appliances such as smartphones, electric car, laptop, etc. the electrochemical cell provides with electrical energy from a chemical reaction [1]. Now, batteries have two main types depending on the fact of rechargeable and non-rechargeable as illustrated in Figure 1. Primary batteries are nonrechargeable and provide electricity as soon as the connection is made with an electrical device’s electrodes. Primary cell can only be used one time, and once they are discharged, they cannot be charged again and are discarded. Some of the examples of primary batteries are Daniel cell, dry cell, zinc air battery, mercury battery, etc. The usage of primary cell includes a wide range of devices like remote controls, pacemakers, toys, and clocks [1], whereas secondary battery is rechargeable and needs to be charged first for providence of energy. Secondary batteries can be used for longer time than primary cells, due to their recharging capability as they can go from 100 to 1000 cycles of charge and discharge. There are numerous examples of secondary batteries, which are magnesium ion battery, nickel zinc battery, sodium ion battery, lithium ion battery, etc. [2]. Lithium ion battery has a higher amount of importance in the industry for a number of reasons. The light weight of Li element, that is, density = 0.53 g/cm3 and the highest electropositive nature in the periodic table has helped in the arranging of battery with high energy density. Still, there are many issues to be addressed for improving the performance [3, 4].
Illustration of (a) alkaline battery as an example of primary battery [5] and (b) general secondary battery [6].
Lithium-ion battery (LIB) is a type of rechargeable battery in which Li ion moves during discharge from the negative electrode (cathode) to the positive electrode (anode) and then during charging Li ions move back from the anode to the cathode. There are four important components: anode, cathode, electrolyte, and separator [3, 4, 7]. Separator has the main role of keeping the electrodes apart, and, to allow the transport of only the charge carriers which in this case are lithium ions [8, 9]. Electrolyte has an important role in the transport as well and is usually made of lithium salts. Whereas, cathodes are made of lithium compounds like lithium cobaltates and lithium phosphates, and anode materials are usually made of 2D materials and their respective compounds. Figure 2 shows a schematic representation of LIBs. When a source is supplied for charging of LIB, Li ions travel from the cathode through the electrolyte and separator to the anode and are intercalated into the 2D material. After fully charged, the source can be removed and the discharging starts in which the Li ions are desorbed from the anode and are transported back to the cathode [10]. The 2D materials that are preferred are graphene and carbon-based compounds because of their high conductivity and Li storage capability, not only on defect-free sites but defective as well [9, 11].
A schematic reperesentation of lithium ion battery [10].
For a long time, the development and creation of new materials have been due to the experimental procedures, which were based entirely upon the intuition and judgment of the experimental researchers, depending upon the facilities as well as the availability of compounds and materials needed for conduction of an experiment. With the passing of time, we have developed computational techniques and codes for investigation of different aspects of a material and how to improve those materials. While the experimental methods are a complete hit in a dark room and waiting for the results to turn out for the best, we can simulate different structures, materials and compounds and alter them to our requirements and desire and then work on how to perform an experiment to get those results. Another way to think is that, when an experiment goes a specific way and we are unable to comprehend the reason, the theoretical calculations and modeling can help us understand on nano and atomic level about the hows and whys. Regarding the lithium ion batteries, there has been a lot of work done to improve its working by studying different materials to be used as a cathode along with studies for improvement of the anode and electrolyte. In this chapter, a brief review of studies made theoretically on nanocarbons for lithium-ion batteries is discussed.
For the analysis of nanostructures, first, a brief general idea of the computational methods is necessary. There are several computational codes and different theoretical backgrounds that are used for these studies. The two main theories are potential-based methods and density functional theory. Here, we will focus on the DFT-based studies and the understanding of the electronic structure. Density functional theory (DFT) is a quantum mechanical approach to the study of the properties of matter on a microscopic basis that is most prevalent and effective [12]. The fundamental principle of DFT is that the total energy of the system is an exclusive functional of the electron density as given by Kohn-Sham equations [13]. The exchange-correlation potential that is introduced into a system helps to calculate the values accurately for which there are several formalisms, like local spin density approximation (LSDA) and generalized gradient approximation (GGA) [14, 15]. Moreover, including the Hubbard potential increases the accuracy of the system as it accounts for the columbic repulsions of the system [16].
The most important part is the simulation of a structure that will complement the experimental procedures. Then, we proceed to see the movement of electrons in these structures and analyze some of the important characteristics, like voltage profile, formation energy, density of states, and diffusion of lithium ion. Here, our focus is on carbon-based compounds, which are mainly used as anodes in LIBs, more specifically graphene structures. Following this the doping, adsorption, heterostructures, cluster systems, composites, and other such possibilities used for enhancement of anode materials are conversed.
One of the important ways to improve the performance of a material is the doping process. Graphene and carbon nanostructures have been doped through various procedures with different elements and studied for use in LIBs. For instance, Yang et al. have done a study on doping of germanium in graphene sheets, resulting in germagraphene and proceeded with observing the adsorption of lithium on different sites. The amount of Li adsorption is shown to be enhanced by doping germanium [17].
Ullah et al. have reported a large capacity anode material for LIBs by doping Be onto the graphene structure and studying the adsorption properties using the SIESTA code [18]. They have simulated single vacancy beryllium doped and double vacancy Be doped graphene structures and then proceeded to study the adsorption of different amounts of Li atoms on top side of the surface as well as bottom side of the surface (Figure 3). The doping of Beryllium makes it an electron-deficient system and the adsorption energy goes to −2.53 eV/Li atom and the rise in the capacity up to 2303.295 mAh/g for the Li8BeC7 structure. The reason for the huge capacitance is that in mono vacancy structure and divacancy structure the Li atoms get attached easily as the doping of Beryllium reduces the electrons and for divacancy the Li adsorption amount is more than mono vacancy.
Li adsorption on Be-doped graphene (top view on left and side view on right): (a) 2 Li atoms with up orientation and (b) 2 Li atoms with down orientation [18].
Proceeding with Be doping, Ullah et al. have done the dual doping of graphene by modeling boron and beryllium, N and Be, and O and Be co-doped structures [19]. Doping of N and O increases the n-type characteristic while doping of B is for p-type characteristic. As Li is adsorbed onto the structures, it is indicated that the BeB doped structure shows good adsorption as the adsorption is ~3.1 times increased. The specification is that B addition increases the p-type nature of the compound that already contains Be and C and hence the Li ion is adsorbed to the dual doped graphene sheet.
A different morphology-based structure was studied recently, in which graphene nanoribbons doped by B and undoped structures were simulated. The adsorption of Li on both the structures was observed which indicated that the capacity increases from 52 to 783 mAh/g when doped with B. The significance of this study is the fact that boron doping in graphene nanoribbons is more effective than the doping into pristine graphene structures [20].
The adsorption of lithium on undoped graphene and N or B doped graphene was studied indicating that the energy of adsorption is highest for Boron-doped graphene and lowest for Nitrogen-doped graphene [21]. The study was performed using the nudged elastic band method and the concentration for doping of both N and B was 12.5 at%, respectively, as shown in Figure 4. The conclusion was that N-doped graphene has better diffusion and desorption qualities than that of pristine graphene and boron doped graphene.
Doped graphene structure (gray color atoms = C and blue color atoms = B or N) [21].
The doping of pyridinic and graphitic nitrogen in a double vacancy graphene structure, that is, 5-8-5 graphene vacancy is studied and the different structures are illustrated in Figure 5 [22]. The potential surfaces, adsorption of 1 Li, adsorption of more than one lithium, and the diffusion of Li across the structure are investigated. Kong et al. have suggested that 4 pyridinic N doped graphene has good adsorption characteristic for Li as well as the diffusion, and hence it will be useful to synthesize for use as anode in LIBs.
(a) Pure graphene, (b) top view of 5-8-5 divacancy graphene, (c) side view of 5-8-5 divacancy graphene, (d) single graphitic N doped graphene, (e) 3 graphitic N doped graphene, (f) 1 pyridinic N doped graphene, (g) 3 pyridinic N doped graphene, and (h) 4 pyridinic N doped graphene [22].
Another point of importance is the amount of nitrogen doping that will be sufficient and what kind of doping will be useful, that is, the sites that are occupied by nitrogen. Yang has studied the nitrogen doping extensively along with the presence of defects and the adsorption of lithium on different structure shown in Figure 6 [23]. The structures include pristine graphene, single N doping, two nitrogen doped at different sites, single nitrogen with single vacancy, and pyridinic structure with single and double vacancy and pyrrolic structure with single and double vacancy. On all these structures the electrical, magnetic, and adsorption properties are studied. The adsorption energy is more for the pristine graphene and single N doped structure while the energy is in negative for all the structures containing vacancies. Furthermore, the magnetic moment is shown to decrease with the adsorption of Li atom by the formation of a bond between free electrons with the electron in Li. Insert figure of structure.
Top and side view of Li adsorbed structures: (a) pristine graphene, (b) single N doped graphene, (c–e) double N doped graphene with diffent sites, (f) single N doped structure with single vacancy, (g–i) three nitrogen doped and single vacancy graphene, (j) double N doped divacancy graphene, and (j) 4 N doped and single vacancy structure [23].
Moreover, Watanabe et al. studied the upper limit for the nitrogen in carbon materials both theoretically and experimentally [24]. In the experimental study, they have concluded that with any increase in the carbonization temperature, the limit for nitrogen content in N doped carbon structures is decreasing. Moreover, the upper limits of N were found to be 14.32 and 21.66 wt% at 1000 and 900, respectively (Figure 7). Then they proceeded with studying the energetically favored structures at 1000 by doping N into C structure. The results they found were in close agreement with their experiment indicating that the existence of doped N in these structures is graphitic.
Graphene structure with varying N/C ratio [24].
Agrawal et al. studied nanocarbon balls and microcarbon balls with and without nitrogen doping, both experimentally and theoretically [25]. Nitrogen doped porous carbon balls had been synthesized in the micro and nano range using the hydrothermal synthesis. According to their work, the nitrogen doped compounds had more electrical conductivity then undoped compounds. Their experimental results showed a similar situation as the charging capacity of N doped structures is more than the undoped micro and nano carbon balls. More recently, N and S co-doped graphene structures were studied theoretically using VASP code [26]. 3N doped graphene, 2N and 1S doped graphene, 1 N and 2 S doped graphene, and 3 S doped graphene structure were simulated with single vacancy site near the doped atoms as shown in Figure 8. It was concluded that the bandgap goes from 0.4473 to 0.255 eV for 3N doped structure and 3S doped structure and that the N on the sited has a negative nature compared to s-doped structure which has a positive structure. With the increasing amount of S atoms, the charge on s decreases and we can tune the properties of graphene from this co-doping for electronic devices like Li-ion batteries.
Single vacancy graphene structures with (a) 3 N, (b) 2 N and 1 S, (c) 2 S and 1 N, and (d) 3 S doping [26].
The theoretical study of Yun et al. on doping of sulfur in graphene nanosheets is a good example of connecting the experiment with calculations and simulations to understand the possibility of sites that are being occupied by a dopant [27]. They have simulated three structures for doping of sulfur in graphene nanosheets as demonstrated in Figure 9. Figure 9a is the adsorption of sulfur on the graphene nanosheet, (Figure 9b) is the substitution of sulfur in the graphene nanosheet, that is, replacing a carbon, and (Figure 9c) is the placement of S2 in a divacancy defect graphene nanosheet. The binding energies for adsorbed sulphur, substitutional sulfur, and S2 divacancy sulfur are 0.85, 7.25, and 4.89 eV, respectively, whereas the bulk sulfur cohesive energy is 2.45 eV. They suggest that substitutional sulfur-doped structure is most likely possibility and that the doping of sulfur contributes to the increase of conductivity in sulfur-doped graphene nanosheet.
Structure of (a) adsorbed S on graphene, (b) substitution of S in graphene, and (c) dimer S2 on divacancy graphene.
Besides the other properties of graphene and carbon nanostructure, it is important for LIBs that the extraction and reinsertion of lithium ion happen smoothly and the resultant is a long-lasting battery. The ionic mobility is an important characteristic; as the material capacitance and other properties improve, for the use of a material as an anode, it is necessary to see the mechanism that is happening in the structure. Adsorption plays an important role along with the doping of the structure.
Zheng et al. provide insight, which shows that in interaction between positive Li ion and graphene, Li ion favors the center of ring position [28]. Their study is based on VASP code and GGA functional. Vacancy-induced structure is also discussed, showing that the vacancy defects decrease the diffusion of positive lithium ion on the surface of the structure. Furthermore, the mechanism of lithiation in pristine graphene and defective graphene was studied by Vivek et al. [29]. They had concluded that the adsorption of Li onto the pristine graphene surface is highly unlikely whereas as the presence of the divacancy and Stone-Wales defects increases the chances of lithiation. As the defects are created, the potential around the defective zone increases which in turn increases the capability of adsorption of Li onto the surface as an adatom. The highest capacity (1675 mAh/g) is seen for the 25% divacancy defect, whereas the highest possibility for Stone-Wales defect at 100% ~1100 mAh/g where the defective structures are shown in Figure 10. A further insight is provided by Zhou et al. who claim that the divacancy defect is more attractive to the Li than the SW defect [30].
(a) Divacancy defect graohene structure and (b) Stone-Wales defect graphene structure [29].
The effect of defects generated in graphene on Li adsorption has been studied in detail with different structure simulations [11, 31]. The formation of lithium clusters on the single vacancy and divacancy defective site was studied by Chen et al. [32]. They have shown the high amount of lithium storage in these defective sites. Mukherjee et al. studied the defective graphene experimentally and theoretically by synthesizing the porous graphene network and simulating it in different divacancy defect percentages [33]. They found their studies to be in agreement and that the Li adsorption had increased around the divacancy defect sites as well as the increasing divacancy defect percentage resulting in increasing lithium storage capacity [33].
The formation of lithium clusters on the (0 0 1) terminated surface suggested that the binding energy is less than that of Li on Li metal [34]. Fan et al. also studied the adsorption of single Li on to the pristine graphene structure and the different possibilities when more than one Li was adsorbed onto the surface that results into a cluster formation. The Li4 is the most stable configuration; as the atoms were placed farther apart, the energy also increases, which is unfavorable. Figure 11 shows the four possible configurations in which Figure 8a is the visualization of the stable state.
Structure of Li adsorbed on graphene (a) Li4 adsorption, (b) single Li at short distance, (c) single Li at slightly more distance, and (d) single Li at the corners of the structure [34].
Modification of graphene to form zigzag edges is explored, which shows that the zigzag edges offer sites for the adsorption of Li and increases the adsorption as compared to pristine graphene or graphite [35, 36]. Furthermore, termination group adsorption onto edge modified graphene and graphite structure was simulated and then the diffusion of Li across these structures had been studied [37]. The termination groups included –O, –H and –OH. Figure 9 shows the charge distribution on the edge modified graphene structure along with the presence of the termination groups on the edge-modified structure. The edge-modification increases the diffusion of lithium across the structure as compared to the pristine graphene. In the terminated structures, the –OH and –H termination decreases the diffusion as compared to the oxygen terminated structure, and from Figure 12 we can see that oxygen has the highest charge contribution.
Charge distribution in edge modified structure: (a) graphene, (b) –H terminations, (c) -OH terminations, and (d) –O terminations [37].
Recently, Si clusters have gained the attention of both experimental and theoretical researchers for different applications. The capability of Si for high Li adsorption when combined with the stability of the graphene or carbon-based materials increases the overall performance of silicon graphene composites [38, 39]. Hu et al. studied the adsorption of Li on a defective graphene surface with silicon cluster already adsorbed [40]. They had simulated various N-doped structures including graphitic graphene, pyridinic graphene, and pyrrolic graphene. After that they proceeded with the different possible configurations of Si adsorptions as shown in Figure 13. Then, Si6 adsorbed structure were observed with Li adsorption, where Li forms bond with Si as along with C. Their study gives a detailed insight about the adsorption of structures where the N-doped defective sites have an important role. Si clusters move towards the defective site, where the volume expansion was decreased because of the defects and makes the adsorption of Li easier.
(a) Si2 cluster adorption on graphitic graphene, (b) Si3 cluster adsorption on graphitic graphene, and (c) Si6 cluster adorption on graphitic graphene [40].
Liou et al. studied the different configurations for adsorption of lithium into a silicon graphene composite and concluded that in graphene silicon composite, intercalation of lithium happening in the interlayer of these two is more stable than the outside [41]. Furthermore, they proceeded with increasing the concentration of graphene layers and silicon percentage and observed that the structures are more stable with the increased concentration of Si [42]. This provides a good insight into the use of Si-incorporated graphitic structures to be used as anodes in LIBs.
2D planar carbon known as popgraphene which is composed of a network of 5-8-5 C rings was shown to be a low energy structure by the bottom-up design [43]. It was reported as an excellent material based on its high adsorption capacity, low diffusion barriers, and its metallic structure because of the attachment of CNTs. Figure 14 shows the adsorption of 12 Li atoms on the popgraphene structure.
Top and side view of pop graphene sheet with Li adsorption (purple = Li atom and gray = C atom) [43].
The formation of heterostructures between carbon-based 2D material graphene and other 2D materials has also been studied for anode applications specifically in the LIB industry. 2D molybdenum oxide MoO2 and graphene heterostructure were studied using the VASP code with GGA [44]. It shows a high theoretical capacity ~1400 mAh/g and high energy density for lithiation and fast charge and discharge rate. Rao et al. studied in detail the monolayer of C2N and the bilayer heterostructure of C2N/graphene [45]. Their results show that the diffusion coefficient for the heterostructure was better than the monolayer after the diffusion of lithium, whereas the capacity of monolayer was 220% the bilayered heterostructure.
The heterostructure of phosphorene and graphene was studied by Wang et al. and showed that the Li intercalation into the phosphorene/graphene heterostructure is better than the pristine phosphorene and pristine graphene [46]. However, there is a small band gap, which indicates the semimetal nature of the phosphorene/graphene heterostructure. Blue phosphorene and graphene heterostructure also shows a similar behavior and high theoretical capacity for lithium intercalation [47]. A bilayer hybrid structure of molybdenum sulfide 2D material with graphene was studied by experimentation as well as simulation [48]. Their purpose was to present a hybrid of these two compounds for lithium storage and concluded that their experimentation is in agreement with the simulation.
A new two-dimensional family of transition metal compounds called MXene and graphene heterostructure were simulated for lithium battery applications [49]. The study includes the intercalation of lithium into many different compounds of MXene as well as MXene and graphene heterostructure in the presence of the functional groups which are –O and –OH terminations attached to MXene as shown in Figure 15. They have established that the stability of the compound is maintained as the lattice parameter and interlayer separation remain almost the same after the intercalation of Li.
(a) and (b) Bi-layer MXene Ti2CTx with intercalated lithium adsorbed (c) and (d) MXene Ti2CTx and graphene with intercalated lithium [49].
Mainly for cathode in LIBs, the compounds used are lithium-based salts, phosphates, etc. Wang et al. have done an extensive study based on simulations as well as experimentations and have proposed structures containing LiFePO4 (LFP) and carbon nanotubes (CNTs) [50]. Their DFT calculations provide a profound understanding of the electrochemical processes. For the DFT study, the structure of CNTs is attached at the (010) interface of LFP and the valence electron cloud charge for the structure is shown in Figure 16. Pure LFP structure has less density of states compared to the structure with CNTs, showing that the electrochemical activity of LFP was enhanced by the attachment of CNTs.
(a) Front-view, (b) side-view, and (c) top-view, for compound interface of LFP and CNTs showing the valence electron cloud distribution [50].
Jiang et al. studied the composite of vanadium oxide with vertically aligned CNT by the synthesis and characterization and then for the mechanism at atomic level the structures were simulated as well [51]. They have simulated CNT, pure vanadium oxide, and then the combination of these two with possible Li adsorption sites as shown in Figure 17. They have concluded that the vanadium oxide inclusion onto the vertically aligned CNT decreases the path for diffusion of Li and aids the adsorption of Li.
Li adsorption on (a) CNT, (b) vanadium oxide, (c) and (d) composite of vanadium oxide on vertically aligned CNT [51].
Cui et al. presented the composite of orthorhombic MoO3 and graphene as a cathode in LIBs with higher conductivity and adsorption of lithium. They studied the structure in bulk form as well as the monolayer structure. They have established that the Li charge and discharge rate have increased in the composite structure along with the capacity of lithium [52].
In conclusion, we can say that the carbon nanostructures are of great importance for use in the LIBs especially as anodes. Nitrogen doping and the various ways in which that is achieved showed very good results. The doping of C-based structures with beryllium, boron, and the co-doping of nitrogen and sulfur gave a different view on the possibilities. The adsorption mechanism of lithium was discussed which gave us a theoretical viewpoint of the procedures that goes on inside the LIBs. Also, the effect of defective sites in graphene structures as well as doped graphene structures on Li adsorption shows that these enhance the lithiation and de-lithiation of Li ion. The heterostructures of graphene with other 2D materials show the many possibilities for experimentation to improve the anode materials.
The authors are thankful to Higher Education Commission (HEC) of Pakistan for providing research funding under the Project No.: 6040/Federal/NRPU/R&D/HEC/2016 and HEC/USAID for financial support under the Project No.: HEC/R&D/PAKUS/2017/783. The author also thanks School of Natural Sciences (SNS) at National University of Science & Technology (NUST), Islamabad, Pakistan for research support.
There are no conflicts of interest.
LIB | lithium ion battery |
DFT | density functional theory |
GGA | generalized gradient approximation |
LSDA | local spin density approximation |
SIESTA | Spanish Initiative for Electronic Simulations with Thousands of Atoms |
VASP | Vienna ab initio simulation package |
SW | Stone-Wales |
CNT | carbon nanotube |
In recent years, many different kinds of materials and techniques have been developed for improved analytical measurements [1, 2, 3, 4, 5, 6, 7]. However, in order to be generally applicable, most materials should have several key properties. These desired properties include, but are not limited to (1) simplicity of preparation (e.g. development involves simply mixing two chemical solutions), (2) tunability (easy introduction of uniform multifunctionality through simple variations), and (3) limited or no toxicity (can be easily designed using materials that are already Food and Drug Administration (FDA) approved). As an example of the latter material, the near infrared (NIR) dye, indocyanine green, for near infrared fluorescence measurements has received early approval by the FDA [7].
On the basis of the above considerations, a wide variety of materials and nanomaterials have been developed and employed for bioanalytical and environmental measurements. In regard to nanomaterials, studies reveal that in general primary properties such as spectra, colorimetric response, and magnetism are size dependent and somewhat tunable. Some of these materials, including carbon dots and silicon dots, exhibit very low cytotoxicities. However, other nanomaterials such as carbon nanotubes and quantum dots have considerably higher toxicities. In some cases, e.g. P-dots and nanogels [8, 9, 10], toxicity depends on the type of polymer used. Aqueous co-ordination complexes are another category of materials and nanomaterials with variable toxicities that have recently been used for analytical and environmental applications [11, 12].
We believe that when one does an exhaustive examination of the literature and considers the inherent properties identified above for improved analytical measurements, a logical conclusion is that ILs, GUMBOS, and nanomaterials derived from GUMBOS (nanoGUMBOS) represent novel classes of materials that best satisfies all of the above properties. Both ILs and GUMBOS are based on use of organic salts. Examples of typical ions used in these salts (ILs and GUMBOS) are shown in Figure 1.
Typical cations and anions used for ILs/GUMBOS production.
These materials are continually being explored for improved analytical measurements. In fact, the literature on development of novel methodologies based on use of ionic liquids (ILs), a group of uniform materials based on organic salts (GUMBOS), and nanoGUMBOS is increasing at an ever-expanding rate. For example, numerous studies from the literature can be cited for utility of such materials in diverse areas such as antibiotics [13, 14, 15], cancer therapy [16, 17, 18, 19, 20, 21, 22, 23, 24], hydrogels [25, 26], cellular imaging [27, 28], chirality [29, 30, 31, 32, 33], dye-sensitized solar cells (DSSCs) [34, 35, 36], extractions [37, 38, 39], gel electrophoresis [40, 41], detection of reactive oxygen species [42], liquid crystals [43], mass spectrometry [44], nanomaterials [45, 46, 47, 48, 49, 50, 51, 52], optoelectronics [53, 54, 55, 56], sensors [57, 58, 59, 60, 61], separation science [62, 63], spectroscopy [64, 65, 66, 67], volatile organic compounds (VOCs) [68, 69, 70, 71, 72, 73, 74, 75], as well as a number of patents and patent applications [76, 77, 78]. Figure 2 provides an abbreviated summary of numerous applications of ILs and GUMBOS.
Applications of ILs/GUMBOS in different research areas.
We note that GUMBOS and nanoGUMBOS are solid phase organic salts (m.p. > 25 °C and < 250 °C) and ILs are typically liquids or low melting solids (m.p. < 100 °C). See Figure 3 below for differentiation between ILs and GUMBOS in terms of melting points. Therefore, some GUMBOS (and nanoGUMBOS) materials fit into the general category of frozen ILs since ILs from 100 °C down to 25 °C are solids. However, many GUMBOS materials are outside the generally accepted temperature range for ILs. Accordingly, a new, more general term of GUMBOS, as defined above, was adopted to apply to this entire class of solid phase organic salts. To date, numerous strategies for this kind of chemistry have been developed. In this chapter, we desire to discuss some of these applications in detail, particularly as applied to the general area of analytical and environmental chemistry.
Melting points range of ILs and GUMBOS.
ILs have been recognized for their properties such as non-volatility, viscosity, negligible vapor pressure, high ionic strength, thermal stability, and low toxicity, among others [79]. As a result of these important properties, ILs were initially designated as green and designer solvents (i.e. first generation ILs) [80]. Eventually, due to their high tunability, new ILs were strategically designed for a variety of functional materials, including lubricants, catalysts, energy materials, etc. [81, 82, 83, 84, 85, 86]. These types of ILs are known as second generation ILs. Finally, major interest has focused on development of new ILs (third generation ILs) for biological applications to achieve biocompatible and low toxic compounds through use of bio-counterions [87, 88]. Moving forward, more attention from the scientific community has focused on development, or recycling of, various molecules into solid phase materials (frozen ILs or GUMBOS) for several biological applications [17, 89, 90, 91]. In this section, the use of frozen ILs and GUMBOS for biological applications such as cancer and antibiotic therapies are discussed.
Cancer is the second leading cause of death in the United States and is a major health concern worldwide [92]. Treatment of cancer typically includes surgery, radiotherapy, hormone therapy, immunotherapy and/or chemotherapy [93]. Effectiveness of these treatments depends upon several factors, such as stage of cancer at the moment of diagnosis, general health of the individual, size and type of tumor, among others. In general, treatment of a person with cancer will involve a combination of therapies as a result of these several factors, and chemotherapy is the most commonly employed treatment [94]. Unfortunately, chemotherapy will often be accompanied with several adverse effects, such as nausea, vomiting, diarrhea, fatigue, malnutrition, anemia, hepatotoxicity, nephrotoxicity, among others [95, 96, 97]. These side effects are the result of high toxicity of typical chemotherapeutic agents that generally lack selectivity toward carcinogenic cells. For all of these reasons, over the past decades major attention has focused on developing new chemotherapeutic agents that are selectively toxic to cancer cells [98, 99, 100]. Moreover, investigations have also focused on early detection methods that involve use of tumor-targeting dyes, as well as near infrared (NIR) dyes for detection, photothermal therapy (PTT) and photodynamic therapy (PDT) [101, 102, 103, 104].
Due to their relatively high division rate and subsequent growth relative to normal cells, cancer cells use more energy [105, 106, 107]. It is well established that the mitochondria are organelles that synthesize adenosine triphosphate (ATP), which is the energy source of cells. As a result, mitochondria in tumor cells have a higher negative mitochondrial membrane potential as compared to normal cells. For this reason, major interest has been directed toward study of cationic compounds as well as positively charged vesicles as chemotherapeutic agents. Several publications from the literature document that these type of compounds are attracted to, and accumulate more selectively, in this organelle of cancer cells, resulting in disruption of ATP synthesis and subsequent induction of cell death [16, 17, 22, 89, 108, 109].
Cationic rhodamine dyes have been studied as mitochondrial targeting agents as early as the 1970s [110, 111, 112, 113, 114, 115]. Furthermore, studies with rhodamine dyes demonstrate that these dyes are toxic to cells above certain concentrations [116, 117]. In contrast, it has been previously reported that hydrophobicity of drugs may improve cellular uptake and distribution inside cancer cells [118]. For this reason, Magut et al. hypothesized that counterion variation in rhodamine 6G dye ([R6G]+) may tune its hydrophobicity [22]. In this regard, four anions: ascorbate ([Asc]−), trifluoremethanesulfonate ([OTf]−), tetraphenylborate ([TPB]−) and bis(perfluoroethylsulfonyl)imide ([BETI]−) were employed to synthesize, through a simple metathesis reaction, four R6G-based GUMBOS. Relative hydrophobicities for each GUMBOS were determined, and the following trend in increasing hydrophobicity from [R6G][Asc] < [R6G][OTf] < [R6G][TPB] < [R6G][BETI] was observed in this study. Clearly, anion variation affected and tuned hydrophobicity, along with other physico-chemical properties, of the parent dye. The low water solubility of these compounds allowed synthesis of nanoGUMBOS through a simple reprecipitation method. In vitro cellular cytotoxicity of these GUMBOS and nanoGUMBOS towards normal breast cells (Hs578T), hormone-independent human breast adenocarcinoma (MDA-MB-231) and hormone-dependent human breast adenocarcinoma (MCF7) cell lines using an MTT assay was evaluated. Interestingly, evaluation of results obtained for [R6G][Asc] and [R6G][OTf] showed that these GUMBOS were highly toxicity toward both normal and cancer cell lines. Similar behavior was observed with the parent compound, [R6G][Cl]. This trend was explained through similar water solubilities of these compounds. In contrast, cytotoxicity results obtained for [R6G][BETI] and [R6G][TPB] indicated that these compounds were more selectively toxic toward cancer cell lines than normal cells. Moreover, these GUMBOS were more toxic against MDA-MB-231 cancer cells, which were the most aggressive cancer cell lines evaluated using 50% inhibition concentration (IC50) values of 11.4 and 12.2 μM for [R6G][BETI] and [R6G][TPB], respectively. Additionally, confocal microscopy studies demonstrated that these nanoGUMBOS were localized inside the mitochondria of cancer cells, which resulted in decreased synthesis of ATP.
Following this study, other researchers focused on evaluating the mechanism of action and internalization of [R6G][BETI] nanoGUMBOS in cells [18]. In that study, Bhattarai and coworkers performed a series of in vitro experiments at different incubation temperatures, in the presence of several endocytic inhibitors, as well as in depletion media, to study internalization of [R6G][BETI] nanoGUMBOS. These experiments allowed the investigators to conclude that these nanoGUMBOS were internalized into cancer cells through a clathrin mediated endocytosis pathway. In contrast, these nanoGUMBOS were found to be internalized in normal cells through an independent endocytic route. Interestingly, it was further demonstrated that [R6G][BETI] nanoGUMBOS passed through lysosome vesicles before reaching the mitochondria. For this reason, Bhattarai and coworkers investigated the integrity of these nanoparticles at lysosomic pH (pH = 4) and normal pH (7.4) values using transmission electron microscopy (TEM) and dynamic light scattering (DLS) experiments. Evaluation of these results demonstrated that nanoparticles lost integrity under acidic pH similar to those in the lysosome, thus releasing [R6G]+ that subsequently entered the mitochondria, and inhibited ATP synthesis and eventually causing apoptosis of cancer cells. Internalization in normal cells did not involve entry through the lysosome. Thus, these investigators concluded that this differential internalization route was the primary reason for selectivity of [R6G][BETI] nanoGUMBOS towards cancer cells. Finally, Bhattarai and co-workers evaluated in vivo efficacy of nanoGUMBOS in tumor size reduction in an athymic nude mouse model. Evaluation of these results demonstrated that nanoGUMBOS inhibited tumor growth and decreased tumors size by 50% making this material a good candidate for in vivo chemotherapeutic applications [18].
It has been previously reported in the literature that there is a strong correlation between size, hydrophobicity, and surface charge of nanomaterials as related to resultant toxicity against cancer cells [119, 120]. Moreover, in vivo studies have demonstrated that nanoparticle size has an important effect in increasing cellular uptake into tumor tissue via leaky tumor vasculature through a phenomenon known as enhanced permeability and retention (EPR) effect [121]. In this regard, Hamdan et al. have shown that use of cyclodextrins (CDs) in nanoGUMBOS synthesis results in more uniform and smaller nanoparticles [45]. CDs are cyclic oligosaccharides having conical shapes, with an inner hydrophobic cavity and an external hydrophilic surface. This characteristic structure of CDs allows interaction with some hydrophobic compounds to provide encapsulation and increased water solubility [122, 123]. For this reason, Bhattarai et al. investigated the synthetic procedure of [R6G][BETI] and [R6G][TPB] nanoGUMBOS in the presence of three different CDs: 2-hydroxypropyl-αCD (HP-αCD), 2-hydropropyl-βCD (HP-βCD), and γ-CD in order to optimize nanoparticle size, uniformity and stability [17]. In this report, nanoparticle synthesis was performed by directly mixing stoichiometric quantities of each parent compound in the presence of predetermined concentrations of each CD until synthetic conditions were optimized. These researchers noticed, from TEM and zeta potential data, that CD-templated nanoparticles presented lower size and higher zeta potentials as compared to control nanoGUMBOS (Figure 4). In Table 1, size, zeta potential and cytotoxicity of CD-templated and control nanoGUMBOS are summarized. Based on evaluation of results obtained using cytotoxicity studies performed with MDA-MB-231 and pancreatic cancer (MiaPaca) cell lines, these researchers noticed a significant decrease in IC50 values, suggesting that CD-templating enhances toxicity of these nanoparticles.
CDs structures and TEM images of [R6G][BETI] nanoGUMBOS in absence and presence of CDs.
Compound | Size (nm) | Zeta potential (mV) | IC50 MDA-MB-231 (μg mL−1) | IC50 MiaPaca (μg mL−1) |
---|---|---|---|---|
[R6G][TPB] control | 105 ± 16 | −23.1 ± 1.2 | 7.3 ± 1.1 | 0.75 ± 0.05 |
[R6G][TPB] HP-α-CD | 55 ± 6 | −27.2 ± 1.5 | 2.6 ± 0.2 | 0.37 ± 0.03 |
[R6G][TPB] HP-β-CD | 44 ± 4 | −29.5 ± 1.1 | 2.7 ± 0.3 | 0.39 ± 0.06 |
[R6G][TPB] γ-CD | 69 ± 6 | −28.3 ± 0.9 | 1.4 ± 0.3 | 0.24 ± 0.04 |
[R6G][BETI] control | 99 ± 12 | −24.3 ± 1.2 | 4.2 ± 0.4 | 0.45 ± 0.05 |
[R6G][BETI] HP-α-CD | 68 ± 8 | −29.0 ± 1.1 | 1.6 ± 0.3 | 0.24 ± 0.03 |
[R6G][BETI] HP-β-CD | 66 ± 4 | −30.1 ± 0.8 | 1.7 ± 0.2 | 0.26 ± 0.04 |
[R6G][BETI] γ-CD | 80 ± 5 | −29.8 ± 1.6 | 2.3 ± 0.4 | 0.30 ± 0.03 |
Size, zeta potential, IC50 for MDA-MB-231 and MiaPaca cell lines for parent and CD-templated nanoGUMBOS [17].
Another approach from this laboratory involved use of an IR-780 dye to synthesize GUMBOS and nanoGUMBOS [16]. IR-780 is a NIR fluorescent dye that has been studied as a possible theranostic agent since it can be employed as an imaging agent as well as a photothermal and photodynamic agent [124, 125, 126]. In this regard, Chen et al. synthesized three IR-780-based GUMBOS through a simple metathesis reaction [16]. Anions evaluated in that study were [Asc]−, [OTf]−, and [BETI]−. Relative hydrophobicity and spectroscopic properties of these GUMBOS were evaluated and compared to the parent compound [IR-780][I]. These researchers found the following hydrophobicity trend: [IR-780][BETI] > [IR-780][I] > [IR-780][OTf] > [IR-780][Asc]. As a result of these larger hydrophobicity values, nanoGUMBOS synthesis was performed through a simple reprecipitation method. Cytotoxicity of [IR-780][BETI] nanoGUMBOS and [IR-780][I] nanomaterials were studied in vitro in three different cancer cell lines: MDA-MB-231, MCF7 and MiaPaca using an MTT assay, and IC50 values were calculated. Interestingly, IC50 for [IR-780][BETI] were lower than IC50 values for nanoparticles of the parent compound for all cell lines evaluated. Furthermore, this [IR-780][BETI] nanoGUMBOS presented the lowest IC50 values against MDA-MB-231, which was the most invasive and aggressive cancer cell line evaluated. These findings indicate that a simple anion variation in a parent compound can selectively change its cytotoxicity towards cancer cell lines.
Relative cell viability was evaluated for each nanoGUMBOS in normal breast cells. These researchers found that all nanoGUMBOS studied were more selectively cytotoxic against cancer cell lines. Results observed after cellular uptake and fluorescence microscopy studies of each nanomaterial allowed these researchers to conclude that nanoGUMBOS, especially [IR-780][BETI], were internalized and accumulated within the mitochondria in higher amounts than with the parent compound. It has been previously reported in the literature that mitochondrial accumulation of [IR-780][I] is followed by cellular apoptosis [127]. In addition, these researchers investigated nanoGUMBOS as inducers of necrosis or mitochondrial disruptors, by employing a mitochondrial toxicity assay. Evaluation of these results showed that nanoGUMBOS presented behavior similar to [IR-780][I] nanomaterials and acted as mitochondrial toxins by inhibiting oxidative phosphorylation. In summary, nanoGUMBOS synthesized in this work represented great potential as possible chemotherapeutic agents along with a strategic advantage as compared to other reported nanomaterials that require complicated synthetic procedures and labels to increase selectivity against cancer cells [128, 129, 130, 131].
In another work, Chen and coworkers evaluated in vitro and in vivo cytotoxicity and photothermal properties of CD-[IR-780][TPB] complexed nanoGUMBOS [89]. In this work, [IR-780][TPB] GUMBOS were synthesized and nanoGUMBOS were obtained in using HP-β-CD. In this case, CD-[IR-780][TPB] nanoGUMBOS represented larger diameters than nanoGUMBOS without CD (Figure 5a and b). These results were different from those obtained by Bhattarai et al. [17], in which CDs acted as a template. Based on analyses of TEM and differential scanning calorimetry results, along with computational modelling, the authors demonstrated that a stable complex was formed between HP-β-CD and [IR-780][TPB]. Afterwards, these researchers performed relative cell viability studies in breast cancer cell lines (MDa-MB-231, MCF-7, and Hs578T) and normal breast cell lines (Hs578Bst and HMEC). Based on these results, Chen and partners demonstrated that CD-[IR-780][TPB] nanoGUMBOS were more selective against cancer cells in comparison to [IR-780][I] nanoparticles and [IR-780][TPB] nanoGUMBOS. Moreover, CD-[IR-780][TPB] nanoGUMBOS were not toxic to breast normal cells in the concentration range evaluated.
TEM images of (a) [IR-780][TPB] nanoGUMBOS, (b) CD-[IR-780][TPB] nanoGUMBOS (scale bar represents 500 nm). (c) In vivo fluorescence of [IR-780][TPB] and CD-[IR-780][TPB] nanoGUMBOS at different time points.
Additionally, cell viability of CD-[IR-780][TPB] nanoGUMBOS were evaluated using MDA-MB-231 and Hs578T cell lines with NIR laser irradiation (808 nm). This resulted in a further decrease in IC50 values for these nanomaterials. Furthermore, these results demonstrate that CD-[IR-780][TPB] nanoGUMBOS represent highly potent chemo- and photothermal therapeutic agents. Finally, Chen et al. also evaluated in vivo efficacy and PTT activity of nanoGUMBOS and CD-nanoGUMBOS using an MDA-MB-231 tumor xenograft model. Interestingly, NIR fluorescence intensity of mice demonstrated that CD-nanoGUMBOS distributed more rapidly and provided a higher tumor accumulation than nanoGUMBOS (Figure 5c). Moreover, these authors observed tumor decrease in mice treated with CD-[IR-780][TPB] nanoGUMBOS plus irradiation. Thus, these results indicated that CD-nanoGUMBOS have great potential as chemo-theranostic agents.
Broadwater et al. combined heptamethine cyanine cation ([Cy]+) with several anions, such as iodide ([I]−), hexafluoroantimonate ([SbF6]−), and hexafluorophosphate ([PF6]−), o-carborane ([CB]−), along with bulkier anions such as tetrakis(4-fluorophenyl)borate ([FPhB]−), cobalticarborane ([CoCB]−), tetrakis (pentafluorophenyl) borate ([TPFB]−), tetrakis[3,5-bis(trifluoro methyl)phenyl]borate ([TFM]−), and Δ-tris(tetrachloro-1,2-benzene diolato) phosphate(V) ([TRIS]−) to obtain several Cy-based organic salts [132]. Redox values, zeta potentials, HOMO energy level, as well as optical properties of all [Cy]-based organic salts were determined in that study. These results demonstrated that counterion exchange allowed tuning of HOMO energy levels of [Cy]+. However, absorbance of all synthesized Cy-based organic salts spectra remained essentially the same.
The above cited authors then synthesized nanoparticles through a simple reprecipitation method. All Cy-based organic salts nanoparticles were determined to have an average size between 5–9 nm and were stable for 22 days. Following these experiments, Broadwater and collaborators evaluated cytotoxicity and phototoxicity of Cy-based organic salt nanoparticles against two different cell lines: human lung carcinoma (A549) and metastatic human melanoma (WM1158) in the absence and presence of 850 nm light. These results indicated that [I]−, [SbF6]−, and [PF6]−, [CB]− presented high cytotoxicity under both condition evaluated, making these compounds good candidates as chemotherapeutic agents. When [Cy]+ was paired with [FPhB]− and [CoCB]− anions, nanoparticles of these compounds were determined to be slightly toxic at concentrations of 7.5 μM without NIR irradiation. However, when these compounds were irradiated with NIR laser, they were highly toxic at 5.5 μM concentrations, which indicates that [Cy][FPhB] and [Cy][CoCB] presented high potential as phototoxic agents. In contrast, compounds where [Cy]+ was combined with bulky anions: [TPFB]−, [TFM]−, and [TRIS]− showed non-cytotoxicity against lung cancer cells. As a result, Broadwater, et al. concluded that these compounds could be employed as imaging agents. Based on cytotoxicity studies, the authors proved that toxicity of [Cy]+ dye was tuned through counterion exchange. Finally, these authors evaluated in vitro imaging properties of all Cy-based organic salts nanoparticles. Analyses of these results demonstrated that non-toxic Cy-based organic salts could be employed at higher concentrations that resulted in a higher fluorescence intensity. Additionally, an in vivo evaluation of these compounds demonstrated that these compounds were accumulated in tumor sites.
Antibiotics were introduced into modern medical practices in the 19th century with the discovery of sulfonamides in the 1930s and penicillin in the 1940s [133, 134, 135]. Without such medication, people often died from infections such as syphilis, gonorrhea, and pneumonia. Thus, use of these antibiotics represented the saving of many thousands of lives and a new era in medicine [136, 137]. Nevertheless, over the years since such discoveries, increased production, indiscriminate use, and over consumption of antibiotics has created an unfortunate outcome of antibiotic and multi-antibiotic resistant bacteria [138, 139, 140]. For this reason, the scientific community has begun to focus on syntheses of new antibiotics that could provide alternative therapies in order to avoid bacterial resistance mechanisms. However, syntheses of completely new antibiotics require great ingenuity, intense synthetic prowess, excellent purification, and considerable resources [141, 142, 143]. As an alternative to the foregoing strategy, several research groups have applied an ion metathesis strategy for antibiotic renewal and enhancement. Thus, recycling of current antibiotics have become a reality.
Florindo et al. synthesized ampicillin based ILs employing triethylammonium ([TEA]+), choline ([N1112OH]+), trihexyltetradecylphosphium ([P66614]+), 1-ethyl-3-methylimidazolium [C2MIm]+, 1-hydroxy-ethyl-3-methylimidazolium [C2OHMIm]+ and cetylpyridinium [C16Pyr]+ as cations to tune crystalline forms and pharmaceutical properties [144]. In that study, water solubility, octanol/water partition coefficient (Ko/w), and phospholipid/water partition (Kp) of synthesized compounds were evaluated. Water solubility of active pharmaceutical ingredients (API) is of great importance because it determines the accessibility and distribution of API within the body. Using water solubility results at room temperature and at 37 °C, the following trend was observed: [C2OHMIM][Amp] > [N1112OH][Amp] > [C2MIM][Amp] > [TEA][Amp]. All Amp-based ILs studied showed lower solubility as compared to [Na][Amp] at room temperature. However, cations with hydroxyl groups presented higher solubility at 37 °C than the parent compound. In contrast, Amp-ILs with longer carbon chains, such as [P66614]+ and [C16Pyr]+, showed Kp values higher than the parent compound, indicating that these compounds could interact better with cellular membranes. Based on results obtained in this study, [N1112OH][Amp] provided the most promising pharmaceutical properties with higher solubility, lower cytotoxicity, lower inflammation response and similar Ko/w relative to the parent compound. Thus, these researchers confirmed that pharmaceutical properties from [Na][Amp] could be finely tuned through simple counterion exchanges.
In another study, the same researchers synthesized ciprofloxacin and norfloxacin fluoroquinolones (FQ) based protic ionic liquids (PILs) through reaction with mesylic acid ([Mes][H]), gluconic acid ([Glu][H]), and glycolic acid ([Gly][H]) to tune their crystalline forms and pharmaceutical properties to enhance their bioavailability [145]. In this case, similar properties as in previous studies were evaluated [144]. The authors observed a clearly increasing trend in aqueous solubility depending on the anion present in FQ-PILs: [Gly]− < [Mes]− < [Glu]−. These observations were in agreement with Ko/w studies obtained by these researchers. Similar Kp results for parent FQs were obtained for their respective organic salts, which indicated that interactions with cellular membranes were not affected. Based on these results, Florindo et al. concluded that FQ-based organic salts studied in this work presented high potential as alternatives to the original antibiotics.
Santos, et al. employed two FQs (ciprofloxacin and norfloxacin) to synthesize active pharmaceutical ingredient (API)-based ILs by combining their salts with the following cations: [N1112OH]+, [C16Pyr]+, 1-ethyl-3-methylimidazolium [C2MIm]+, 1-hydroxy-ethyl-3-methylimidazolium [C2OHMIM]+, 1-(2-hydroxyethyl)-2,3-dimethylimidazolium [C2OHDMIm]+, and 1-(2-methoxyethyl)-3-methylimidazolium ([C3OMIm]+) [146]. Water solubility of the synthesized compounds were evaluated, and the following trend was observed: [EMIM]+ < [Ch]+ < [C2OHDMIM]+ ≈ [C3OMIM]+ < [C2OHMIM]+. This trend was similar to results reported in a previous study from the same group [145]. The authors determined IC50 concentrations of these FQ-ILs in this study against three bacteria: Bacillus subtilis (B. subtilis), Staphylococcus aureus (S. aureus) and Klebsiella pneumoniae (K. pneumonia) and compared results with IC50 values of the parent compounds. In order to evaluate if the synthesized compounds were more effective than the parent compounds, these researchers calculated the relative decrease of inhibitory concentration (RDIC) obtained by divided the minimum inhibitory concentration (MIC) values of each API-ILs by MIC of the corresponding API. Interestingly, most compounds evaluated in this work presented better antimicrobial activity than the original FQ with RDIC values higher than one [146].
Frizzo et al. employed sodium ibuprofen ([Na][Ibu]) and sodium docusate to synthesize API-based ILs [147]. Sodium cations in the parent compounds were replaced with ranitidine ([Ran]+), diphenhydramine, glycine, or glycine ethyl cations. In this work, these researchers tested all synthesized compounds along with parent compounds against several types of bacteria and species of Candidas fungus. Evaluation of their results demonstrated that, in general, all API-ILs presented better antifungal activity than the precursors. For example, all ibuprofen-based ILs demonstrated antifungal activity. Interestingly, [Ran][Ibu] ILs presented antifungal activity when the parent compounds did not. In contrast, most API-ILs presented higher antibacterial activity than the parent compounds. These researchers synthesized ibuprofen- and docusate- based ILs that demonstrated high potential as antimicrobial and antifungal agents.
Ferraz et al. [148] also employed amoxicillin ([seco-Amx]−) and penicillin G ([seco-Pen]−) in combination with imidazolium, choline, ammonium, phosphonium and pyridinium cations to synthesize antibiotic based API-ILs. Resistant and sensitive Gram positive and Gram negative bacteria, including methicillin resistant S. aureus (MRSA ATCC 43300), were employed to test antimicrobial efficacy of these API-ILs through use of a broth micro dilution method. Evaluation of results obtained on sensitive strains demonstrated that only three of all evaluated compounds [C2OHMIM][seco-Amx], [C2OHMIM][seco-Pen], and [TEA][seco-Pen], produced lower or equal MIC values than the parent compounds and RDIC values equal to or higher than one. However, more interesting results were obtained when these compounds were tested against resistant bacteria such as Escherichia coli (E. coli) strains CTX M9 and CTX M2 as well as methicillin-resistant S. aureus ATCC 43,300. When tested against resistant E. coli, [C16Pyr][seco-Amx] presented the highest RDIC value (> 100). In contrast, [C16Pyr][seco-Amx] and [C16Pyr][seco-Pen] were more effective against S. aureus ATCC 43,300 with RDICs higher than 1000 and 100, respectively. Another compound that was more effective than the commercial antibiotic was [N1112OH][seco-Pen] with RDIC larger than 5. These findings clearly demonstrate that [C16Pyr]+ cation played an important role in antimicrobial activity of synthesized API-ILs acting in a synergetic way along with API present in the compound [148].
Cole and coworkers proposed recycling of antibiotics into GUMBOS [15]. In this work, ampicillin based GUMBOS (Amp-GUMBOS) were synthesized through a simple metathesis reaction where a sodium cation was replaced by hexadecyl-methyl-imidazolium ([C16MIm]+), hexadecyl-dimethyl-imidazolium ([C16M2Im]+) and [C16Pyr]+. These Amp-ILs were tested against Gram negative and positive bacteria and compared to parent compounds. Interestingly, MIC values obtained for Amp-GUMBOS in these experiments demonstrated that these concentrations were between 2 to 43 times lower than MIC values determined for ampicillin.
Following their previous studies, Cole and co-workers employed chlorhexidine and ampicillin to synthesize antibacterial GUMBOS [14]. These two antibacterial agents are commonly used in veterinary practices to treat and/or prevent the presence of E. coli strains that are commonly found in cattle. The presence of E. coli strains could produce severe illness in humans, especially E. coli O157:H7, which is well-known because it produces bloody diarrhea, haemorrhagic colitis and haemolytic uraemic syndrome in humans [149, 150, 151]. For this reason, development of a prophylactic treatment for this type of bacteria are highly desirable for eradication or minimization in cattle to prevent human illnesses. Cole et al. evaluated the efficacy of this Chlorhexidine di-ampicillin GUMBOS to kill several E. coli O157:H7 strains isolated from different sources such as chicken, pork, beef, apple cider, burger and humans [14]. Chlorhexidine di-ampicillin GUMBOS was found to kill E. coli strains more effectively since these GUMBOS presented MIC values much lower than the parent compounds and their unreacted stoichiometric mixture. Moreover, interaction indices indicated that this antimicrobial GUMBOS presented a synergetic mechanism effect. Chlorhexidine is a commonly used antiseptic; however, it presents high cytotoxicity against normal cells. For this reason, these researchers studied cytotoxicity of GUMBOS, parent compounds and unreacted stoichiometric mixtures in Hela cells. Interestingly, GUMBOS were less toxic than parent chlorhexidine, reaching 93% cell viability.
In another work, Cole and coworkers recycled four β-lactam antibiotics (ampicillin, cephalothin, carbenicillin and oxicilin) into GUMBOS, by combining them with chlorhexidine diacetate [152]. Twenty-five bacteria isolates were obtained from several sources, where most of these were resistant or multi-resistant to antibiotics. These four β-lactam – based chlorhexidine GUMBOS were tested against these isolates. Results obtained by Cole and coworkers demonstrated that these β-lactam – based chlorhexidine GUMBOS were more effective against these isolates with MIC values in a range between 0.1 to 32 μM as compared to parent compounds with higher MIC (5 to >1250 μM). Moreover, in this report Cole et al. evaluated if these GUMBOS presented a synergetic, additive or antagonist effect relative to their unreacted mixtures of stoichiometric equivalents. Interestingly, these researchers found that for most GUMBOS studied, the observed effect was synergetic [153].
Neisseria gonorrhoeae is another bacterial target that is primarily sexually transmitted and responsible for the disease gonorrhea [154]. In recent years, N. gonorrhoeae resistance to current treatments have been isolated and reported around the world [155, 156]. Lopez et al. have synthesized GUMBOS from an antiseptic octenidine and a discontinued antibiotic carbenicillin as a possible alternative to reduce and minimize N. gonorrhoeae transmission [157]. The zone of inhibition (ZOI) for N. gonorrhoeae strains and clinical isolates were studied in the presence of GUMBOS, parent compounds, and antibiotics currently employed for gonorrhea treatment. Evaluation of results obtained demonstrated that synthesized GUMBOS presented an additive effect as compared to the parent compounds as well as an equivalent antimicrobial activity like azithromycin.
Sensing strategies for a variety of systems, from biological targets [158], environmental and regulatory applications [159, 160], mechanical integrity of structures [161, 162, 163], and more [60, 164], are continuously under investigation in the scientific community. In general, recognition can be categorized into two different methodologies: targeted and non-targeted [165]. Targeted strategies require materials that are designed to respond to specific analyte(s) and thus, require a high degree of specificity for singular analytes [63, 160, 166]. Differential strategies, however, can potentially provide information within convoluted and complex mixtures based on several non-specific sensors or one sensor with multi-layered responses to different analytes [167]. In the following sections, solid-state ionic materials for various sensing applications are discussed.
Previous investigations using fluorescent imaging with solid-state ionic materials have undergone scrutiny to prevent or reduce self-quenching between dye molecules in order to enhance properties such as excitation energy transfer and achieve on/off switching in nanoparticle structures [168, 169, 170, 171, 172, 173]. Traditionally, dye self-quenching has been rectified by introducing bulky side-chains into the molecular structure via synthetic organic chemistry [173, 174, 175]. However, this type of strategy requires several synthetic and purification steps that result in increased expense. In contrast, large counterions were observed to also inhibit this self-quenching phenomenon in a much more facile manner through a simple ion metathesis reaction [28, 50]. Several research groups have capitalized on this strategy to study polymeric nanoparticle encapsulated rhodamine-derived GUMBOS, respective photophysical properties, and cellular uptake ability for imaging applications along with targeting agents to provide organelle contrast [28, 173, 176, 177].
More recently, researchers have diversified beyond cellular imaging techniques. For example, Severi et al. have explored polymer encapsulation of nanoprobes that undergo efficient Förster resonance energy transfer (FRET) for potential point-of-care applications with smartphones [178]. In this study, ester-modified cations rhodamine 110 and 6G cations ([R110]+ and [R6G]+, respectively) were employed as FRET donor dyes with bulky tetrakis[3,5-bis(1,1,1,3,3,3-hexafluoro-2-methoxy-2-propyl)phenyl]borate trihydrate ([F12]−) and tetrakis(perfluoro-tertbutoxy)aluminate ([F9-Al−]) counterions [177]. These Ion pairs were encapsulated with DNA cancer marker (survivin) targeted polymer nanoparticles, which were also functionalized using a red-emitting oligonucleotide-functionalized dye as a FRET acceptor. After nanoparticle size, quantum yield (QY), FRET acceptor concentration optimization, and evaluation of FRET capabilities, encapsulated [R6G][F9-Al] nanoprobes were evaluated for red, green, blue (RGB) survivin DNA marker detection in solution using fluorescence spectroscopy. These researchers found that their designed system had a limit of detection of 3pM. Upon optimization of microscopic and digital imaging, these researchers also found that using an iPhone SE, [R6G][F9-Al] as an encapsulated FRET donor in their designed nanoprobe allowed a 10pM limit of detection. Thus, these researchers demonstrated that [R6G][F9-Al] was successfully employed as a visualization agent for potential development of a point of care ratiometric imaging method.
In another study, McNeel et al. expanded upon counterion metathesis by synthesizing a strategic three-component nanoGUMBOS compound for selective imaging of breast cancer cells [27]. Two of three components selected were dianionic fluorescein ([FL]2−) and cationic rhodamine B ([RhB]+), which could undergo pH-dependent FRET [179]. These researchers approached their triple-GUMBOS synthetic design through pH manipulation with [FL]2−, rhodamine B chloride [RhB][Cl], and [P66614][Cl] as a hydrophobic agent, to yield [P66614][RhB][FL] triple GUMBOS. The resultant compound was then employed for nanoGUMBOS synthesis, and when precipitated from water with neutral pH, nanoparticles of approximately 4.4 nm ± 0.7 nm were obtained. However, when using other pH values for nanoGUMBOS synthesis, these researchers determined that nanoGUMBOS sizes and size distributions varied. Absorbance and fluorescence emission properties from low to high pH values were reported, and noticeable ratiometric changes in spectra were observed. A linear ratiometric trend corresponding to pH-dependent FRET responses was observed between moderate pH values (approximately pH 5.0 to 7.0), from which quantitative information may be derived. To further demonstrate the applicability of this three-component nanoGUMBOS system, these investigators also conducted fluorescence microscopy imaging studies with normal and cancerous breast cells. These studies demonstrated that nanoGUMBOS maintained clear selectivity for breast cancer cells since, as cells were illuminated. In contrast, normal cells remained dim. Therefore, three-component nanoGUMBOS were determined useful for both pH sensing and fluorescence imaging of breast cancer cells without the use of polymer encapsulation [27].
Another application for FRET-based sensing of solid-state ionic materials is described by Ashokkumar et al. [180]. In this work, oxygen sensing nanoparticle probes for cellular systems were developed using a polymer encapsulated novel cyanine dye called [BlueCy]+ tetrakis(pentafluorophenyl) borate ([F5-TPB]−) or [BlueCy][F5-TPB] that was also loaded with oxygen sensing platinum octaethylporphyrin (PtOEP) as a FRET acceptor. In this case, [BlueCy]+ was designed as FRET donor and synthesized from two cyanine dyes: 2-methyl-3-octadecylbenzo[d]thiazol-3-ium iodide and 3-methyl-2-(methylthio)benzo[d]thiazol-3-ium iodide. After dye encapsulation into poly(methyl methacrylate-co-methacrylic acid) and poly(lactic-co-glycolic acid), PMMA-MA and PLGA, respectively, it was determined that both dyes were successfully incorporated into PMMA-MA. Nanoparticle sizes, PtOEP loading, and photophysical properties were evaluated. These investigators determined that dye encapsulated PMMA-MA nanoparticles were 40 nm in diameter with 17% QY after reprecipitation from dioxane. Moreover, after testing several ratios of donor dye loadings, ratios of 1:100 (PtOEP:[BlueCy][F6-TPB]) demonstrated good FRET efficiency. Solution based experiments for oxygen sensing were performed, and ratiometric trends were demonstrated for oxygen rich and poor environments. After confirming low phototoxicity when incubated with HeLa cells, the investigators conducted further studies with FRET nanoparticles in low and normal oxygen environments. HeLa cells were incubated with FRET nanoparticles in a microfluidic device, and an oxygen gradient was introduced by application of an oxygen scavenger. Resultant emission gradients were observed after fluorescent microscopic images were obtained. Ultimately, these researchers demonstrated the utility of their nanoprobe for detection of cancer cells via microfluidic application. As a result, the authors concluded that this probe could also be used to visualize oxygen gradients in cancerous cells.
In another study from the Warner research group, nanoGUMBOS were synthesized and evaluated as ratiometric sensors for reactive oxygen species (ROS) [42]. Cong et al. designed binary nanoGUMBOS using reprecipitation of 1,1′-diethyl-2,2′-cyanine and 1,1′-diethyl-2,2′-carbocyanine bis(perfluoroethylsulfonyl) imide ([PIC][NTf2] and [PC][NTf2], respectively). Optimal FRET efficiency was determined to be 10:1 [PIC]:[PC] molar ratio, and binary nanoparticles shapes were classified as nanodiamonds with spectrally consistent J-aggregation. Analysis of variance (ANOVA) was employed to investigate reactivity of ROS with nanoGUMBOS. Significant differences were observed for hydroxyl radical (•OH) over four other evaluated ROS, indicating selectivity of this binary nanoGUMBOS system toward •OH species. Moreover, these investigators observed a linear trend for ratiometric sensing of this probe at various concentrations of •OH in the presence of singlet oxygen (1O2). Further, potential applications in imaging were investigated, nanoGUMBOS were incubated with breast cancer cells and exposed to oxidative stress. Fluorescence emission changes before and after oxidative stress indicated results in agreement with solution-based studies. Therefore, a binary ratiometric nanoGUMBOS probe was developed for potential quantitative ROS imaging studies using a facile method.
Biosensing of mixtures of biomarkers and/or proteins is of particular interest for disease diagnosis and treatment [181, 182, 183]. Many current methods, such as enzyme-linked immunosorbent assay (ELISA) or polyacrylamide gel electrophoresis (PAGE) coupled to mass spectrometry, require expensive resources and labor intensive steps [183, 184, 185]. Organic salts are of increasing interest for development of fluorescent sensor arrays for protein detection and discrimination as they are easily tunable for increasing hydrophobicity, traditionally more stable upon ion exchange, and require little resources for purification [90].
Galpothdeniya and coworkers used partially selective 6-(p-toluidino)-2-naphthalenesulfonate sodium salt ([TNS][Na]) in an ion exchange metathesis reaction with cations tetrabutylphosphonium ([P4444]+), benzyltriphenylphosphonium ([BTP]+), 4-nitrobenzyltriphenylphosphonium ([4NBP]+), and tetraphenylphosphonium ([TPP]+) in order to obtain four different GUMBOS [59]. These investigators rationalized that, as a result of partial selectivity to hydrophobic regions of proteins, TNS-based GUMBOS would make facile, suitable candidates to generate a sensor array for proteins. Proteins such as human serum albumin (HSA), fibrinogen, α-antitrypsin (α-Ant), immunoglobulin G (IgG), β-lactoglobulin (β-Lac), ribonuclease A (RNaseA), α-chymotrypsin (α-CTP), transferrin (Trans), lysozyme (Lys) were used for sensor array development. Sensor responses were collected at various concentrations of proteins.
As a result of notably larger sensor responses, [TNS]-based GUMBOS were determined to have highest sensitivity to HSA, α-Ant, and β-Lac proteins. For this reason, the investigators employed responses for sensor responses to different concentrations of HSA, α-Ant, and β-Lac for multivariate analysis. Both sensor response values and corresponding protein concentrations were employed to build a principal component analysis (PCA) model. By employing the first two principal components (PCs), which accounted for 99.72% of the variance, a linear discriminant analysis (LDA) model with cross-validation was constructed reaching 100% discrimination accuracy. These researchers noted that the highest sensor responses were obtained for HSA and α-Ant. Thus, these sensor responses were employed to generate anther PCA model in order to evaluate discrimination between these two proteins regardless of protein concentration. In this model, the first two PCs accounted for 99.91% variance, and LDA with cross-validation resulted in 91.7% accuracy. To improve this accuracy, these investigators normalized sensor responses for each protein, constructed a PCA model with the first three PCs corresponding to 98.29% variance. These three PCs were employed for LDA construction and, with cross-validation, accuracy resulted in 100% discrimination. Furthermore, five mixtures of different HSA: α-Ant ratios were evaluated for mixture discrimination analysis. In this case, PCA followed by LDA resulted in 100% discrimination accuracy. Thus, TNS-GUMBOS were evaluated and confirmed as useful materials for protein sensor arrays for analyses of serum proteins HSA, α-Ant, and β-Lac.
More recently, Pérez and coworkers developed a nanoGUMBOS sensor array based on three fluorescent thiacarbocyanine ([TC0]+, [TC1]+, and [TC2]+) dyes with two anions ([BETI]− and [NTf2]−) for discrimination of several proteins [183]. NanoGUMBOS and microGUMBOS of these six compounds varied in size and shape, from circular shapes with [TC0][NTf2] and sizes around 25 nm, to [TC1][BETI] with rod-like shapes and an average size of 1.2 ± 0.5 μm by 0.21 ± 0.08 μm, and [TC2][NTf2] displayed triangular profiles with average dimensions 200 ± 10 nm by 177 ± 80 nm. Aggregates of nanoGUMBOS of [TC0]- and [TC2]-GUMBOS exhibited absorbance spectral characteristics representative of H-aggregation, while [TC1][NTf2] and [TC1][BETI] both resulted in spectral peaks representative of J-aggregation.
In the above study, seven proteins were investigated, including the four most abundant serum proteins: HSA, IgG, transferrin (Trans), and fibrinogen (Fib), along with three non-serum proteins hemoglobin (Hb), cytochrome C (CytC), and lysozyme (Lys), with each protein exhibiting different physical characteristics. The investigators observed different response patterns for each protein. In this work, these researchers determined that employing raw data was optimal for constructing an LDA model, in which 100% discrimination accuracy of proteins was achieved. Among different protein concentrations, sensor responses were determined to be stable between 0.1 to 20 μg/mL. Mixtures of two proteins, HSA and Hb, were also investigated in this work. Various weight ratios of HAS:Hb mixtures from 100% HSA to 100% Hb, were evaluated and 100% accuracy was achieved when LDA was constructed using these response patterns. However, 80:20 HSA:Hb was observed to be an outlier with the lowest canonical score values, and further analysis using hierarchical cluster analysis determined this dataset to be less related to other ratios. Protein spiked artificial urine with 5 μg/mL protein concentration was employed to evaluate sensor array performance in real samples, and LDA model performance achieved 100% discrimination accuracy. Thus, a series of TC-based GUMBOS were successfully synthesized into nanoGUMBOS and microGUMBOS and developed as protein sensor arrays capable of 100% discrimination in complex mixtures.
ILs have been explored for quartz crystal microbalance (QCM) applications as chemosensors for detection and discrimination of volatile organic compounds (VOC) [186, 187, 188, 189]. However, for these investigations, differentiation of VOCs sensor response relied on concentration and molecular composition of an analyte. In 2012, Regmi and coworkers developed a system to correlate sensor responses using GUMBOS-polymer composite [75]. In this work, investigators characterized and explored the responses of cellulose acetate and 1-butyl-2,3-dimethylimidazolium hexafluorophosphate (CA-[BM2IM][PF6]). By carefully evaluating characteristic responses upon exposure to control sensors, composite material, and confirming results using molecular dynamic simulations, investigators determined that sensor response recorded as changes in frequency were directly proportional to changes in motional resistance. Thus, these researchers successfully derived molecular weight trends from their composite sensor.
Another exploration demonstrated that counterion exchange using only GUMBOS coatings on quartz crystal resonators (QCRs) could provide VOC differentiation. In 2015, Regmi et al. explored trihexyltetradecylphosphium copper phthalocyanine-3,4′,4″,4″’-tetrasulfonic acid ([P66614]4[CuPcS4]) and trihexyltetradecylphosphium copper(II) meso-tetra(4-carboxyphenyl)porphyrin ([P66614]4[CuTCPP]) as sensing materials [73]. Each GUMBOS sensor successfully allowed detection of a variety of VOCs, such as acetone, acetonitrile, nitromethane, toluene, chloroform (CHCl3), methanol (MeOH), ethanol (EtOH), 2-propanol, 1-propanol, 1-butanol, and 3-methyl-1-butanol. Both sensor responses readily allowed detection of multiple alcohols at relatively low detection limits when compared to other polar and nonpolar analytes. When compared to IL trihexyltetradecylphosphium bis(trifluoromethanesulfonimide), [P66614]4[CuTCPP] provided higher frequency response signals upon exposure to MeOH vapor, and more rapidly achieved baseline with efficient replicate results. Thus, these investigators demonstrated that use of copper(II) porphyrin counterion in GUMBOS allowed investigators to achieve high selectivity in sensor responses to VOCs [73]. Since these reports, there have been other explorations into IL and/or polymer-IL composite responses for VOC detection, and many have attained discrimination via statistical techniques to access virtual and multi-sensor arrays [69, 70, 71, 72, 190].
Since VOCs are frequently found as complex mixtures, Vaughan et al. have proposed development of a multi-sensor array (MSA) employing copper(II) phthalocyanine or [CuPcS4]-based GUMBOS sensors [68]. An example of such a sensory coating scheme is shown in Figure 6. VOCs studied represent compounds from different classes, such as dichloromethane (DCM), MeOH, 1-propanol, toluene, CHCl3, heptane, hexane, and benzene. In this work, [P4444]+, tributyl-n-octylphosphonium ([P4448]+), tetrabutylammonium ([TBA]+), 3-(dodecyldimethyl-ammonio)propanesulfonate ([DDMA]+) were employed as cations for [CuPcS4]4− to generate four different sensory coatings. Each coating displayed different layering characteristics as determined by SEM. Upon exposure to VOCs, each sensor presented analyte specific response patterns. Using original data, and quadratic discriminant analysis (QDA) with cross-validation, the resultant accuracy was determined to be 98.6%. Thus, [CuPcS4]-based GUMBOS responses were successfully employed to build a VOC-MSA to achieve high accuracy discrimination [68].
(a) Representative example of GUMBOS coated QCR; (b) analyte sensing and harmonic wave pattern of QCR on electrode surface.
With increasing global commercialization of state-of-the-art optoelectronic displays, the demand for higher performance and flexible materials has also increased [108, 109, 110, 111]. In general, these devices are comprised of emissive layers between electrodes along with several other electronically active layers. Organic light emitting diodes (OLEDs) and organic photovoltaics (OPVs) have been the central target for a multitude of research groups, from organic emissive layer development to full device performance [108, 109, 110, 111, 112]. Counterion strategies using cations and anions within active layers for enhancement on optoelectronic device fabrication to effects on emission and device function will be discussed in the following sections.
Scientists have optimized several characteristics for targeted OLED development where they require consistent uniformity of emissive layers for potential manufacturing production [191], low crystallinity to prevent non-linear optical activity [192, 193], resistance to oxidation and water [194], and high thermal stability and optical purity [195]. Ionic transition metal complexes (ITMCs) are of huge interest as a wide range of emissive hues is easily achievable, synthesis is relatively simple, and they have desirable luminescent properties [196]. However, traditional methods of OLEDs fabrication involves vacuum evaporation deposition, or vacuum thermal evaporation (VTE) [197], which involves uniform coating of emissive layers [198].
In this regard, Dongxin Ma and coworkers have investigated four cationic iridium complexes as candidates for VTE through counterion control [196]. By incorporating large non-coordinating anions, these investigators achieved VTE iridium-based ionic emissive layers. The anions [PF6]−, [TPFB]−, and tetrakis[3,5-bis(trifluoromethyl)phenyl]borate ([BArF]−) were employed for quantum chemical calculations, and the investigators determined that distances between iridium and boron atoms were larger than 8 Å with both [TPFB]− and [BArF24]− counterions. In comparison, distances between iridium and phosphorous was determined to be 6 Å, as a result of a larger partial positive charge on the phosphorous atom. Compounds synthesized from metathesis with bulkier anions [TPFB]− and [BArF24]− were employed for device fabrication using VTE as larger interatomic distances were presumed more suitable for phase transition, and device performance was evaluated. These investigators found devices ranged from blue to red-orange with external quantum efficiencies (EQEs) ranging from 1.2% (blue emission) to 8.1% (yellow emission) [196]. In 2018, these anions were also employed to produce two red-orange devices based on cationic iridium compounds, and these compounds were useful as dopants in 4,4′,4″-tris(carbazol-9-yl)triphenylamine emissive layers (TCTA) to produce white OLEDs with Commission Internationale de L’Eclairage (CIE) coordinate values equal to (0.33, 0.34), that were near to the required values (0.33, 0.33) [199].
More recently, Bai and coworkers investigated counterion-tuning strategies for a sky-blue fluorescent Ir-cation for VTE [200]. Instead of boron-based anions to improve VTE, the investigators strategically focused on bulky sulfonate-containing anions that also contained electron-deficient oxadiazole and triazine structures, such as 3,5-bis(5-(4-(tert-butyl)phenyl)-1,3,4-oxadiazol-2-yl)benzenesulfonate ([OXD-7-SO3]−), 4-(4,6-diphenyl-1,3,5-triazin-2-yl)benzenesulfonate ([TRZ-p-SO3]−), and 3-(4,6-diphenyl-1,3,5-triazin-2-yl)benzenesulfonate ([TRZ-m-SO3]−). These structures were expected to not only provide VTE capabilities, but also improve carrier transport and trapping efficiencies that would improve overall efficiency and blue-emission of OLEDs. These researchers concluded that devices fabricated with [TRZ-m-SO3]− and [TRZ-p-SO3]− anions resulted in better overall device performances, slightly decreased CIE x-coordinate value, and displayed the largest external quantum efficiencies (EQEs) of 12.3 and 12.4%, respectively [200].
Carbazole-containing compounds with expanded conjugation are known to provide efficient blue emission, although they often require high labor and resource costs. In this regard, Siraj et al. synthesized carbazole imidazolium iodide ([CI][I]) along with analogues containing [OTf]−, [NTf2]−, and [BETI]− anions as respective GUMBOS in an efficient manner [54]. These GUMBOS were then compared to parent [CI][I] to evaluate counterion effects on thermal and photochemical properties that relate to performance for blue-emitters for OLEDs. In this study, non-uniform packing was observed in all GUMBOS as a result of cation structure. All ion-exchanged GUMBOS also demonstrated significantly higher thermal stabilities with onset degradation temperatures ranging from 310 to 417 °C as determined by thermal gravimetric analysis (TGA), where increasing size of anion yielded increased degradation temperature ([I] < [OTf]− < [NTf2]− < [BETI]−). Similarly, QYs were increased with ion exchanges. In methanolic solution, [CI][BETI] was determined to have the largest QY of 99%, followed by [CI][OTf] with 94%, [CI][NTf2] with 73%, and [CI][I] with 25%. Thus, this demonstrated that hydrophobic counterion exchange affects photophysical properties of the CI-cation.
While VTE has dominated OLED manufacturing, it often requires expensive equipment and is both energy and time consuming [201]. For this reason, several researchers have explored solution processing methods, such as spin coating [201], electrospray deposition [54], along with other methods [202, 203] to provide faster, more inexpensive fabrication procedures [204]. In this report, [CI][OTf], [CI][NTf2], and [CI][BETI] GUMBOS were used to fabricate thin films on quartz glass with electrospray deposition [205], and uniform coating was achieved and confirmed by scanning electron microscopy and fluorescence microscopic analysis. Solid-state emission spectra displayed very slight red-shifting from methanolic spectra of ion-metathesis GUMBOS. In addition, photostabilities were investigated, and [CI][BETI] displayed an irradiation-induced increase in photostability. In contrast, [CI][OTf] and [CI][NTf2] were relatively stable while irradiated for 3000 s. Moreover, cyclic voltammetry and quantum chemical calculations further supported spectral properties of evaluated CI-based GUMBOS.
In 2016, Zhang and coworkers designed a novel cyanopyridinium stilbene cation ([Py]+) in order to examine the influence of counterion effects on solid-state photophysical properties [206]. Chloride ([Cl]−), nitrate ([NO3]−), tosylate ([OTs]−), and [TPB]− anions were employed in this study to form Ion pairs, and the resultant compounds showed little fluorescence in solution. When explored as films, blue-shifting of emission peaks occurred and increased with increasing hydrophobicity of counterions; QYs also increased following this trend. However, [Py][TPB] GUMBOS were non-emissive in solid-state. In order to understand this variance in trend, investigators used X-ray crystallography and quantum chemical calculations. From these studies, the authors determined that dimeric fluorophore aggregates were responsible for emission in GUMBOS. In [Py][TPB], fluorophores became dilute as a result of bulky anions, resulting in very weak fluorescence emission. This was also confirmed in quantum chemical studies, where intramolecular charge transfer characteristics were confirmed through prediction of frontier molecular orbital placement to reveal donor-σ-acceptor properties for dimeric stacking.
In another study, expansion of applications of the propidium dication ([P]2+) was investigated by exchanging iodide counterions for [OTf]−, [NTf2]−, and [BETI]− anions to generate P-based GUMBOS for potential solid-state applications [53]. Thermal, spectral, photo-physical, computational, and electrochemical properties were investigated for all P- based GUMBOS. While [P][OTF] retained physical properties similar to parent dye, such as solubility in more polar solvents, thermal degradation, and higher relative crystallinity, similar to the parent compound. In contrast, [P][NTf2] and [P][BETI] GUMBOS were more soluble in hydrophobic solvents, more amorphous, and displayed higher thermal stability. A trend was observed where increasing solvent hydrophobicity increased fluorescence lifetime and QY values. The highest fluorescence lifetime and QY for [P][BETI], followed by [P][NTf2], was observed in DCM. In this regard, the authors proposed that this effect may be a result of hydrophobic counterion stabilization of excited-state [P]2+, a phenomenon that resembles the original sensing behavior of the parent compound [P][I] [207]. These investigators also performed cyclic voltammetry to determine oxidation and reduction potentials for each P-based GUMBOS, as well as solution-phase QY calculations. It was determined through computational experiments that electronic transitions would lead to an increased propensity for torsional twisting in the solid state [208]. From these studies, the authors concluded that by simple counterion exchange, applications for propidium dication may be expanded beyond biological probes to potential candidates in optoelectronic devices [53].
Dye-sensitized solar cells (DSSCs) are an emerging next-generation technology in OPVs [209]. Through intrinsic characteristics such as natural transparency, good efficiency in low light conditions, flexible substrate production and more, applications may be expanded to windows, indoor fixtures, and wearable electronics [210, 211]. Incorporation of two or more complementary sensitizing dyes allows for potential absorption of all wavelengths of sunlight to achieve much higher power conversion efficiencies (PCEs) [209, 212, 213, 214, 215]. When implemented in this field, tunable investigations of co-sensitizing dyes that are also ionic and primarily limited to structural variations of zwitterionic squaraine-heptamethine structures rather than ion pairs [216, 217]. Polymethine, or cyanine dyes, however, have been extensively studied in OPV technologies, and several groups have begun explorations into counterion application in DSSCs [218, 219, 220, 221, 222, 223].
In 2012, Jordan et al. from the Warner research group reported synthesis and characterization of [PIC][NTf2] and [PIC][BETI], along with fabrication of respective nanoGUMBOS [36]. Optical properties were compared to the parent [PIC][I], and nanoGUMBOS were synthesized and characterized using TEM and scanning electron microscopy (SEM). Optical properties of the resultant PIC-based nanoGUMBOS were also investigated. These investigators concluded that [PIC][NTf2] nanodiamonds resulted in a significant increase in fluorescence emission intensity, which could be a result of J-aggregation. The authors hypothesized that [PIC][BETI] nanorods from H-aggregates only slightly increased fluorescence intensity. In 2014, Sarkar and coworkers investigated morphology, size, and current–voltage characteristics of these PIC-based nanoGUMBOS using atomic force microscopy (AFM) and conductive probe-AFM (CP-AFM) [56]. Results from CP-AFM indicated that when the voltage was swept between 1 and − 1 Volts, current values within the range of approximately 10−7 to 10−8 Amps could be achieved. Raman spectroscopy was employed to monitor anion effects on aggregation changes via changes in intensity. These researchers confirmed that [PIC][NTf2] nanoGUMBOS exhibited J-aggregation while H-aggregation was observed in [PIC][BETI] nanoGUMBOS. Thus, researchers from both investigations showcased anion dependent nanoparticle morphology and respective effects on spectral and electrochemical properties of broadly absorbing PIC-based nanoGUMBOS that had potential uses in DSSCs.
Kolic et al. have investigated different GUMBOS, including the aforementioned PIC-based GUMBOS, to determine effects on DSSC performances [34]. These dyes were employed as energy relay dyes (ERDs) in electrolyte solutions, where FRET occurs to donate electrons from ERD molecules in electrolyte solution to photosensitizing dye at the electrode surface. Figure 7 represents a proposed scheme for electron transfer processes involving GUMBOS-ERDs DSSCs. Photoactive dyes such as rhodamine B ([RhB]+), [PIC]+, thiacarbocyanine ([TC1]+), and tetracarboxyphenylporphine ([TCPP]4−) precursors underwent ion exchange with appropriate counterions, such as [NTf2]−, [BETI]−, and [P66614]+, and were further evaluated for counterion effects on ERD performance. Among various GUMBOS studies, investigators determined that [RhB][NTf2] and [P66614]4[TCPP] GUMBOS yielded most promising PCEs devices. These investigators hypothesized that this was a result of inherent high molar extinction coefficients and QYs for these respective compounds. They also noted that devices employing [NTf2]− anions resulted in higher respective device efficiencies than those of the parent dye or [BETI]− anions. One deviation of this trend, however, was the case of [TC1][TPB], which demonstrated a much higher QY. Overall, these authors were able to elucidate anion trends for GUMBOS-ERDs and confirm their utility as FRET cosensitizing agents in DSSCs [34].
Schematic of DSSCs fabricated with GUMBOS-ERDs and potential operational mechanism [34, 209].
Other works have recently focused on incorporating metal-based GUMBOS as redox shuttles for sensitizer regenerating agents in DSSCs as well. In 2016, Huckaba and coworkers employed a cobalt(II/III) redox shuttle ([Co(bpy)3]2+/3+) with [NTf2]− as a non-coordinating anion with indolizine sensitizers [224]. Device PCEs ranged from 3.04 to 8.10% efficiencies, which were comparable to employing common redox shuttle, iodide/triiodide (I−/I3−) (3.74–7.99%). Additionally, a copper(I/II) redox shuttle ([Cu(tmby)2]+/2+) with [NTf2]− counterion was recently employed with indoline derivatives as sensitizers [225]. This study determined that this redox system rapidly regenerated indoline dyes within the range of tens of nanoseconds, several orders of magnitude faster than cobalt(II/III) shuttle [Co(bpy)3]2+/3+[NTf2]3/2 [225]. As a result of the volatility of the organic solvent employed in electrolyte solutions, some groups have expanded investigations into non-volatile routes for DSSC fabrication [212, 226, 227]. Cao and coworkers have developed a solid-state DSSC (ssDSSC) based on [Cu(tmby)2]+/2+[NTf2]2 redox shuttle for a hole transport layer [228]. In comparison to other copper redox shuttles, PCEs were determined to be much higher with this novel ssDSSC at 11% versus 4.5 or 2%, respectively. Thus, using their trilayered approach with co-sensitizer (Y123) and their solid-state hole transport material, scientists successfully demonstrated charge separation in a novel ssDSSC.
Work function (WF) is a metric by which charge transfer at electrodes is measured to determine electron injection efficiencies of optoelectronics [229]. For this reason, many groups have targeted improving device efficiency by optimizing charge transport at interfacial layers by including electroactive coatings[229, 230, 231]. Incorporating ethoxylated polyethylenimine (PEIE) at electrode interfaces of OLEDs was previously demonstrated by Zhou and coworkers to reduce WF [232]. In 2019, Ohisa et al. hypothesized that incorporation of tetraalkylammonium salts ([TRA][X]) into PEIE layers could further reduce required WFs for OLEDs [232, 233]. Alkyl chain lengths that varied between tetraethyl ([TEA]+), tetrabutyl ([TBA]+), and tetrahexyl ([THA]+) ammonium groups were studied in this report. Different anions were employed, and a series of salts were investigated for each ammonium cations. Anions employed ranged from [Cl]−, bromine ([Br]−), [I]−, acetyl ([Ac]−), thiocyanate ([SCN]−), or tetrafluoroborate ([BF4]−). Ultimately, 30 wt % [TBA][X] incorporation into PEIE layer at cathode interfaces improved WF as determined by ultraviolet photoelectron spectroscopy [233]. Researchers determined that anions with strong electron donating characteristics, such as [SCN]− and [Ac]−, resulted in the largest reduction of WF, while small halides provided the lowest WF change.
Investigators continued their investigations with chain length studies using [TEA][Cl] and [THA][Cl] dopants in PEIE electrode coatings and studying WF values. Results indicated that longer chain lengths provided larger steric hindrance, and thus, weaker electron accepting ability. Overall, WF decreased as hypothesized; however, devices with PEIE:[TBA][SCN] doping resulted in an unexplained increase in drive voltage. In general, this work demonstrates anion influence on WF and electronic efficiencies in LEDs [233]. More recently, Duan and coworkers expanded this work to include anion exchange effects on polyelectrolytes inspired by PEIE design [234]. These investigators incorporated ammonium cations into the PEIE backbone and used several sulfonate anions, such as dimethyl sulfonate ([MSB]−), benzylsulfonate ([BSB]−), and diethyl sulfonate ([ESB]−), to examine effects on WF for polymer solar cells. Notably, these researchers found that smaller anions, e.g. [ESB]− and [MSB]−, yielded devices with more efficient electron transport characteristics and better performance than devices with [BSB]−. Interestingly, devices with [PEIE][ESB] demonstrated the highest PCE (10.44%) with 8 nm thickness at minimal light soaking [234].
In another work, Sato and coworkers investigated counterion exchange effects on a polymerized IL system to reduce WF at the electron-injection layer to provide sufficient electrons to the semiconducting layer [232]. These investigators employed two fluorinated anions to produce polydiallylammonium polymeric ILs [poly(DDA)][NTf2] and [poly(DDA)][BETI], respectively. Both polymers were evaluated and compared to their parent PIL [poly(DDA)][Cl]. Hydrophobicities were studied via water contact angle measurements between film samples and water droplets. As anticipated, larger contact angles were observed for the more hydrophobic anions [NTf2]− and [BETI]− as compared with [Cl]−, 80.1, 80.8 and 19.1o, respectively. Noticeable increases in 5% onset degradation temperatures of the polymers were also observed upon conversion from PIL to polymer-ion exchanges, from 285 °C in [poly(DDA)][Cl] to 394 and 395 °C with [poly(DDA)][NTf2] and [poly(DDA)][BETI], respectively. Both ion-exchanged polymer-ILs reduced WF when they were incorporated at the cathode interface and increased WF when employed at the anode, which indicates that they are suitable interfacial coatings for OLED development. After device optimization as electron injection layers, the authors reported a best device performance of 9.00% maximum EQE with [poly(DDA)][NTf2]. Overall, these researchers demonstrated the benefits of hydrophobic counterion exchange for PILs and their utility for OLEDs applications at electrode interfaces.
Much like room temperature ILs, the ionic properties of frozen ILs and GUMBOS lend to high tunability as a result of the exponential combinations possible of known anions and cations. This important characteristic allows for strategic design of specific GUMBOS for a targeted analytical task. This chapter summarized a few examples of possible GUMBOS applications. Moreover, it has been demonstrated that several physico-chemical properties of these compounds are improved in solid state as compared to liquid phase organic salts. For these reasons, we hypothesize that implementation of solid-phase ILs and GUMBOS in the analytical and materials fields will increase in the future.
The authors gratefully acknowledge financial support through NASA cooperative agreement NNX 16AQ93A under contract number NASA/LEQSF (2016-2019)-Phase 3-10, and the National Science Foundation under Grant Nos. CHE-1905105 and HRD-1736136. Any opinions, findings, and conclusions or recommendations expressed in this material are those of the author(s) and do not necessarily reflect the views of the National Science Foundation.
The authors declare no conflict of interest.
IntechOpen is the first native scientific publisher of Open Access books, with more than 116,000 authors worldwide, ranging from globally-renowned Nobel Prize winners to up-and-coming researchers at the cutting edge of scientific discovery. Established in Europe with the new headquarters based in London, and with plans for international growth, IntechOpen is the leading publisher of Open Access scientific books. The values of our business are based on the same ones that any scientist applies to their research -- we have created a culture of respect, collegiality and collaboration within an atmosphere that’s relaxed, friendly and progressive.
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