Binding constants, K1,1 in dm3 mol−1, for the inclusion complexes CD/APG.
\\n\\n
Released this past November, the list is based on data collected from the Web of Science and highlights some of the world’s most influential scientific minds by naming the researchers whose publications over the previous decade have included a high number of Highly Cited Papers placing them among the top 1% most-cited.
\\n\\nWe wish to congratulate all of the researchers named and especially our authors on this amazing accomplishment! We are happy and proud to share in their success!
\\n"}]',published:!0,mainMedia:null},components:[{type:"htmlEditorComponent",content:'IntechOpen is proud to announce that 179 of our authors have made the Clarivate™ Highly Cited Researchers List for 2020, ranking them among the top 1% most-cited.
\n\nThroughout the years, the list has named a total of 252 IntechOpen authors as Highly Cited. Of those researchers, 69 have been featured on the list multiple times.
\n\n\n\nReleased this past November, the list is based on data collected from the Web of Science and highlights some of the world’s most influential scientific minds by naming the researchers whose publications over the previous decade have included a high number of Highly Cited Papers placing them among the top 1% most-cited.
\n\nWe wish to congratulate all of the researchers named and especially our authors on this amazing accomplishment! We are happy and proud to share in their success!
\n'}],latestNews:[{slug:"stanford-university-identifies-top-2-scientists-over-1-000-are-intechopen-authors-and-editors-20210122",title:"Stanford University Identifies Top 2% Scientists, Over 1,000 are IntechOpen Authors and Editors"},{slug:"intechopen-authors-included-in-the-highly-cited-researchers-list-for-2020-20210121",title:"IntechOpen Authors Included in the Highly Cited Researchers List for 2020"},{slug:"intechopen-maintains-position-as-the-world-s-largest-oa-book-publisher-20201218",title:"IntechOpen Maintains Position as the World’s Largest OA Book Publisher"},{slug:"all-intechopen-books-available-on-perlego-20201215",title:"All IntechOpen Books Available on Perlego"},{slug:"oiv-awards-recognizes-intechopen-s-editors-20201127",title:"OIV Awards Recognizes IntechOpen's Editors"},{slug:"intechopen-joins-crossref-s-initiative-for-open-abstracts-i4oa-to-boost-the-discovery-of-research-20201005",title:"IntechOpen joins Crossref's Initiative for Open Abstracts (I4OA) to Boost the Discovery of Research"},{slug:"intechopen-hits-milestone-5-000-open-access-books-published-20200908",title:"IntechOpen hits milestone: 5,000 Open Access books published!"},{slug:"intechopen-books-hosted-on-the-mathworks-book-program-20200819",title:"IntechOpen Books Hosted on the MathWorks Book Program"}]},book:{item:{type:"book",id:"3394",leadTitle:null,fullTitle:"Arthroplasty - Update",title:"Arthroplasty",subtitle:"Update",reviewType:"peer-reviewed",abstract:"New technologies, developments in implant design and advances in surgical technique have improved outcomes after joint replacement and decreased rate of complications. It is not a surprise that the number of arthroplasties increases steadily every year and nowadays more than one million patients undergo the procedure annually worldwide. This book is a sequel of a successful series dedicated to one of the fastest growing fields in orthopedics - arthroplasty. Aiming at dissemination of scientific research this book provides a profound overview of the recent evolution of technology and surgical techniques. New developments of implant design and current treatment strategies have been critically discussed by the contributing authors. The process of improving care for patients and standards of treatment requires straightforward access to up-to-date research and knowledge. The format of the publication allows easy and quick reference to shared ideas and concepts. We hope, that the current book will add significant contribution to the success of this endeavor.",isbn:null,printIsbn:"978-953-51-0995-2",pdfIsbn:"978-953-51-7096-9",doi:"10.5772/56149",price:159,priceEur:175,priceUsd:205,slug:"arthroplasty-update",numberOfPages:620,isOpenForSubmission:!1,isInWos:1,hash:"672aa53986638f5846f76ee8c8a1ea9e",bookSignature:"Plamen Kinov",publishedDate:"February 20th 2013",coverURL:"https://cdn.intechopen.com/books/images_new/3394.jpg",numberOfDownloads:81192,numberOfWosCitations:29,numberOfCrossrefCitations:23,numberOfDimensionsCitations:64,hasAltmetrics:1,numberOfTotalCitations:116,isAvailableForWebshopOrdering:!0,dateEndFirstStepPublish:"May 2nd 2012",dateEndSecondStepPublish:"May 23rd 2012",dateEndThirdStepPublish:"August 27th 2012",dateEndFourthStepPublish:"November 25th 2012",dateEndFifthStepPublish:"December 25th 2012",currentStepOfPublishingProcess:5,indexedIn:"1,2,3,4,5,6",editedByType:"Edited by",kuFlag:!1,editors:[{id:"64690",title:"Prof.",name:"Plamen",middleName:null,surname:"Kinov",slug:"plamen-kinov",fullName:"Plamen Kinov",profilePictureURL:"https://mts.intechopen.com/storage/users/64690/images/system/64690.jpg",biography:"Assoc. Professor Plamen Kinov, MD, PhD, is a Head of Joint Replacement Unit at Department of Orthopedics, Medical University of Sofia, Bulgaria, with his scientific interests focused on hip and knee replacement.\nHe graduated medicine with honors in 1995 at the Medical University of Pleven, Bulgaria and completed his training in orthopedics at Medical University of Sofia, Bulgaria.\nHe was a research fellow at the Department of Orthopedics, University of Graz, Austria and a visiting fellow in Graz, Austria, Munich, Germany, and Bologna, Italy. \nHe was awarded International Society of Orthopedic Surgery and Traumatology (SICOT) Abdel Hay Mashhour Award and Bulgarian Orthopedics and Traumatology Association (BOTA) Award. He is an author of over 120 scientific publications.\nHe is a Treasurer of the Bulgarian Orthopedics and Traumatology Association (BOTA) and was a Secretary of BOTA and an Editorial Secretary of Bulgarian Journal of Orthopedics and Traumatology. Plamen Kinov is a member of European Federation of National Associations of Orthopedics and Traumatology (EFORT), American Academy of Orthopedic Surgeons (AAOS), European Hip Society (EHS), among other scientific societies.",institutionString:null,position:null,outsideEditionCount:0,totalCites:0,totalAuthoredChapters:"2",totalChapterViews:"0",totalEditedBooks:"1",institution:{name:"Medical University of Sofia",institutionURL:null,country:{name:"Bulgaria"}}}],equalEditorOne:null,equalEditorTwo:null,equalEditorThree:null,coeditorOne:null,coeditorTwo:null,coeditorThree:null,coeditorFour:null,coeditorFive:null,topics:[{id:"1150",title:"Orthopedics",slug:"orthopedics"}],chapters:[{id:"42802",title:"Surgical Approaches to the Hip Joint and Its Clinical Implications in Adult Hip Arthroplasty",doi:"10.5772/55212",slug:"surgical-approaches-to-the-hip-joint-and-its-clinical-implications-in-adult-hip-arthroplasty",totalDownloads:5951,totalCrossrefCites:0,totalDimensionsCites:1,signatures:"Hiran Amarasekera",downloadPdfUrl:"/chapter/pdf-download/42802",previewPdfUrl:"/chapter/pdf-preview/42802",authors:[{id:"67634",title:"Dr.",name:"Hiran",surname:"Amarasekera",slug:"hiran-amarasekera",fullName:"Hiran Amarasekera"}],corrections:null},{id:"43073",title:"Preoperative Planning of Total Knee Replacement",doi:"10.5772/55023",slug:"preoperative-planning-of-total-knee-replacement",totalDownloads:5023,totalCrossrefCites:0,totalDimensionsCites:3,signatures:"A.O. 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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:"59189",title:"Interactions between Bio-Based Compounds and Cyclodextrins",doi:"10.5772/intechopen.73531",slug:"interactions-between-bio-based-compounds-and-cyclodextrins",body:'Due to its structure, cyclodextrins (CDs) readily form inclusion complexes through noncovalent interactions with molecular guests. The lipophilic cavity of CDs provides a microenvironment into which appropriately sized nonpolar moieties can enter. The hydrophobicity of the cavity enables the accommodation of a broad range of hydrophobic guests such as the alkyl chains of surfactants or different phytochemicals [1]. The hydrophilic exterior usually imparts CDs and their complexes, considerable solubility in water. The charge and polarity of the guest molecule play also an important role in the CD-substrate host-guest interaction [2]. However, this aspect is obviously less important than the geometric fitting. In the case of the charge, the complexation of neutral molecules is easier than the ionized counterpart. In general, molecules can be encapsulated by CDs when they are less hydrophilic or less polar than the solvent and when the formed complex is stable.
The main driving force for the formation of the complex is the release of enthalpy-rich water molecules from the cavity; water molecules are displaced by more hydrophobic guest molecules present in the solution to achieve the apolar-apolar interactions and decrease of CD ring strain resulting in a favorable lower energy state. The beneficial modification of guest molecular properties after the formation of the inclusion complex leads to a large number of applications in areas as diverse as encapsulation of active substances (i.e., flavoring agents, metallic cations, fragrances, and pesticides), enzymatic synthesis, catalysis, and energy transfer studies [3, 4]. Additionally, CDs also find important uses in cosmetics, environment protection, bioconversion, packing, textiles, and food domain [1, 5].
Less than 10% of all produced CDs and CD derivatives are used by the pharmaceutical industry. The largest CD users are the food and the cosmetic industry. CDs have a high level of biocompatibility, are absorbed in the gastrointestinal tract, and are completely metabolized by the colon microflora [6]. Some of them are approved by the Food and Drug Administration or have been accredited as being “generally recognized as safe” (GRAS) [7]. In the cosmetic area, CD performance stands out in the following: solubilize and stabilize specific sensitive components, stabilize emulsions, improve the absorption of active components onto the skin, reduce or eliminate bad aromas from certain components, and reduce the loss of the active components through volatilization, rapid oxidation, destruction by light, etc. [8].
Plants are a remarkable source of biologically active compounds with potential applications in cosmetic, pharmaceutical, and food industries. Among the bioactive compounds synthesized as secondary metabolites by plants, phenolic compounds are probably the most relevant ones. Physiologically, they play a vital role in plant protection and contribute to plant odors, plant pigmentation, and/or their flavors. Structurally, phenolic compounds have, at least, one aromatic ring, with one or more hydroxyl groups attached [9]. The great diversity of phenolic compounds present in nature (i.e., more than 8000 different structures have been identified up to now) results from variations in the basic chemical skeleton (e.g., degree of oxidation, hydroxylation, methylation, glycosylation, and conjugation with further molecules, particularly lipids, proteins, other phenolics, and biomolecular metabolites) [9]. Phenolic compounds are grouped by the number of phenol rings they contain and the structural elements that bind these rings to another; flavonoids, phenolic acids, tannins, stilbenes, and lignans are examples of important representatives of these groups [10].
On the other hand, plant essential oils (EOs) are mixtures of numerous highly complex volatile compounds (hydrogenated and oxygenated monoterpenes, sesquiterpenes, phenols, simple alcohols, ketones, coumarins, etc.) present in variable concentrations whose aroma depends on the individual constituents present [11]. Due to their natural properties, EOs have been used as therapeutic remedies and flavoring agents since ancient times. In the last decades, many investigations showed that EOs have a wide range of valuable biological activities, such as antimicrobial, herbicidal, insecticidal, antioxidant, etc.
Although many investigations demonstrated the broad range of biological activities of many phytochemicals, they still have restricted applicability as pharmaceuticals or in food products due to their poor water insolubility and bioavailability, high volatility, rapid oxidation, or degradation when exposed to environmental factors. New approaches have been developed to overcome these drawbacks, and among them, CDs have been suggested as excellent vehicles for the protection of phytochemicals for food and drug delivery proposes [12, 13, 14].
According to a recent review by Suvarna et al., there are many phytochemicals whose solubility, bioavailability, or therapeutic activity is significantly improved by complexation with CDs (e.g., quercetin, curcumin, artemisinin, resveratrol, naringenin, etc.) [12]. The methods used for the formation of inclusion complexes between CDs and bioactive compounds are essentially neutralization, slurry, solution, coprecipitation, kneading, and grinding [15].
The encapsulation of phytochemicals with CDs usually involves the formation of 1:1 inclusion complexes with the most versatile CD, the β-CDs, and its derivatives. These derivatives can be classified according to their interaction with the water molecules in hydrophilic, hydrophobic, and ionizable derivatives [13]. Examples of used hydrophilic β-CDs are the methylated β-CDs—2,6-dimethyl-β-CD (DM-β-CD) and 2,3,6-trimethyl-β-CD (TM-β-CD)—the hydroxyalkylated β-CDs such as 2-hydroxypropyl-β-CD (HP-β-CD), and the branched β-CDs, glycosyl-β-CD (G-β-CD). These molecules are suitable for the formation of host-guest inclusion complexes with poor water-soluble compounds. On the other hand, the hydrophobic derivatives, such as the alkylated β-CD 2,6-diethyl-β-CD (DE-β-CD), are used to decrease and modulate the released rate of water-soluble molecules. Finally, the ionizable β-CD can enhance the dissolution rate and the inclusion capacity and even decrease the side effects of some molecules [16, 17]. Among the ionizable CDs, O-carboxymethyl-β-CD (CM-β-CD), O-carboxymethyl-O-ethyl-β-CD (CME-β-CD), and sulfate and sulfobutylether-β-CD (SBE-β-CD) should be highlighted.
Owing to their potential health promotion effects particularly the antioxidant, anti-inflammatory, and antimicrobial properties, one of the actual promising applications of phenolic compounds is their use in the food industry as additives, e.g., in the development of functional foods. Nevertheless, the efficacy of these natural compounds is dependent on the preservation or improvement of their stability, bioactivity, and bioavailability [18]. Inclusion complexation with CDs improves water solubility of phenolics and enhances their shelf life and biological activity [15]. Additionally, it has been shown that the inclusion of phenolic compounds (e.g., hydroxycinnamic and chlorogenic acids) with CD (β-CD) strongly limited their interactions with proteins, which is important regarding the use of phenolics as food additives [19, 20]. Note that the interactions of these compounds with proteins, frequently added to functional foods to improve nutritional value and proper texture characteristics, often decrease the bioavailability of both proteins and phenolics [21].
There are many examples showing that the complexation of β-CD, or some of its derivatives, increases the biological activity of phenolics. For instance, Shao et al. observed that the complexation of chlorogenic acid (CGA) with CDs (β-CD and HP-β-CD) improved its antioxidant activity [22]. Moreover, the addition of CGA-CD complexes to grape juice reduced the degradation of anthocyanins due to copigmentation effect with the CGA/HP-β-CD complex showing the superior activity and copigmentation effects. Gabaldon et al. also used HP-β-CD to increase the aqueous solubility of kaempferol, quercetin, and myricetin and to improve their antioxidant activity due to the protection toward free radical attack [23]. The complexation of curcumin with an ionizable β-CD (SBE-β-CD) enhanced its water solubility and, thus, improved the in vitro cytotoxic (on HepG-2 cells) and antioxidant activity of these compounds [24]. This β-CD derivative and the HP-β-CD are the most used derivatives on the pharmaceutical industry due to their low toxicity and high solubility [16, 25, 26].
EOs can be regarded as mixtures of phytochemicals, and there are several studies reporting the complexation of EOs or their components with CDs mainly to overcome problems related with EO water insolubility, high volatility, rapid oxidation, heat damage, and degradation on exposure to air [14]. Although many studies focus the complexation of EO components with β-CDs or its derivatives, e.g., eugenol/HP-β-CD [27] and linalool/HP-β-CD [28], it has been observed that sometimes γ-CD is a better complexing agent. Ciobanu et al. showed that menthol, menthone, and pulegone are capable to form stable 1:1 inclusion complexes with β-CD, but eucalyptol forms a more stable inclusion complex with γ-CD due to the size of its cavity [29]. Polymeric CDs, which can be synthesized using cross-linking agents such as epichlorohydrin, also revealed promising results in some specific cases but are not matter of discussion in this chapter [29].
The inclusion complexes of EOs (or their components) with CDs have been mainly tested for food and pharmaceutical applications, but they could be an efficient tool to improve the use of EOs in aromatherapy, cosmetic, and household cleaning products. An interesting application of EOs is related to their incorporation in food packaging systems or edible films due to their antimicrobial, antioxidant, and insect repellent capacity. However, this is often limited due to flavoring and organoleptic considerations. CD inclusion complexes could overcome these limitations allowing EOs to reach effective concentrations in the food matrices without exceeding organoleptically acceptable levels and even providing controlled release-rate kinetics. Recent studies encourage the use of CD-EO (e.g., β-CD/Satureja montana EO; γ-CD inclusion complex encapsulated electrospun zein nanofibrous webs/thymol) complexes as part of active packaging systems [30, 31] as well as promising candidates to be used as safe and effective antimicrobial agents (β-CD/eugenol) to control postharvest diseases in fruits [27].
There are scientific evidences that inclusion complexation with CDs improves the pharmacological effects of EOs or their components [28, 32, 33]. For instance, the complexation of Hyptis pectinata L. EO with β-CD improved its analgesic effect in a mice model [34]. Also Bomfim et al. observed that β-CD complexation increased in vivo tumor growth inhibition capacity of Annona vepretorum EO [32]. Recently, Lima et al. reviewed the preclinical and clinical studies published on complexes between CDs and terpenes [33]. These are the major components of EOs that exhibit a wide range of biological activities on the human body. Their survey shows that there is robust experimental evidence that CDs improve the oral absorption and pharmacological properties of terpenes. Nevertheless, more pharmacokinetic and clinical studies are required before they can be effectively used in clinical targets.
Despite the production of surfactants based on fats, oils, and carbohydrates, being a known area for several decades, on an industrial scale, this is a relatively new issue [35]. These amphiphilic molecules that have one of the main building blocks from a natural source are often called “natural surfactants” [36, 37]. For example, alkyl glycosides which are synthesized from a “natural” sugar unit and a “nonnatural” fatty alcohol are often regarded as natural surfactants. Considering their amphiphilic nature, it has been always a challenge to attach a carbohydrate molecule, such as the hydrophilic group (due to the numerous hydroxyl groups) to a fat and oil derivative, such as a fatty acid or a fatty alcohol. However, nowadays, several successful synthesis routes are well established, and numerous types of natural surfactants are known and available, even on a commercial scale [38]. Nowadays, carbohydrate-based surfactants (CBS) are among the most important classes of amphiphilic compounds [39, 40, 41]. Their structure results from the combination of sugar and lipids, naturally biosynthesized within living cells or, alternatively, synthetically prepared by sequential reactions using carbohydrate and fatty materials. The growing interest in such compounds is due to, inter alia, their preparation from renewable raw materials, biodegradability, mildness to the skin, and biocompatibility, among other reasons [42, 43]. In particular, CBS can be relatively easily prepared from the most abundant renewable vegetable raw materials (e.g., cellulose, pectin, hemicellulose, starch, etc.) in a wide range of structures and geometries by modular synthesis thanks to the presence of numerous reactive hydroxyl groups. Such structural diversity makes CBS excellent models to get insight on the surfactant mechanisms in modifying interfacial properties. This knowledge is crucial for the control of the formation and stability of diverse colloidal systems such as micelles, vesicles, foams, and emulsions [44]. An important structural feature of these surfactants is the typical sugar headgroup, a voluminous and relatively rigid moiety that can be functionalized by a myriad of reagents and synthetic schemes. Numerous properties and functionalities can be expected from such almost unlimited number of different compounds that can find specific applications in different industrial areas [45, 46]. CBS also present great advantages on the environmental side; their higher biodegradability and lower toxicity profile are important reasons to consider CBS as valid alternatives to the more common petrochemical-based surfactants.
In recent years there has been a growing focus on three classes of surfactants with sugar or a polyol derivative as polar headgroup: alkyl polyglycosides (APGs), alkyl glucamides, and sugar esters. In this chapter, we will focus on APGs, which are regarded as “perfect amphiphilic structures” with excellent surface activity as well as solubility. APGs have been synthesized, for the first time, more than 100 years ago [47]. APGs are completely based on renewable resources and combine very good performance, multifunctionality, and competitive price with mildness. This explains why APGs are the most successful sugar-based surfactants nowadays. It is important to mention that not pure alkyl monoglucosides but rather a complex mixture of alkyl mono-, di-, tri-, and oligoglycosides is produced in the industrial processes. Because of this, the industrial products are called alkyl polyglycosides. The surfactants are thus characterized by the length of the alkyl chain and the average number of glucose units linked to it, the degree of polymerization (DP). Alkyl glycosides are stable at high pH and sensitive to low pH where they hydrolyze to sugar and fatty alcohol. The sugar unit is more water-soluble and less soluble in hydrocarbons than the corresponding polyoxyethylene unit; hence, APGs and other polyol-based surfactants are more lipophobic than their polyoxyethylene-based surfactant counterparts [48]. This makes the physicochemical behavior of APG surfactants in oil/water systems distinct from that of conventional nonionic surfactants. Moreover, APGs do not show the pronounced inverse solubility vs. temperature relationship that normal nonionics do [49]. This makes an important difference in solution behavior between APGs and polyoxyethylene-based surfactants. The critical micelle concentration (cmc) values of the pure alkyl monoglycosides and the technical APG are comparable with those of typical nonionic surfactants and decrease distinctly with increasing alkyl chain length. The alkyl chain length has a far stronger influence on the cmc than the number of glycoside groups of the APG. The influence of the DP of APGs on their phase behavior has been described by Fukuda et al. [50]. The region in which the liquid crystalline phases occur is only slightly dependent on the concentration with a greater expansion in the case of APGs with a higher DP.
Regarding their applications, APGs are mainly used in personal care products such as cosmetics, manual dishwashing, and detergents [51]. APGs have also been used in more advanced applications such as the extraction and purification of membrane proteins, which plays a major role in the determination of protein structures and functions [52]. This is because APGs have reduced protein-denaturing properties in comparison to conventional surfactants. Generally, the environmental fate of surfactants is inextricably linked with their biodegradation behavior. Thus, fast and complete biodegradability is the most important requirement for an environmentally compatible surfactant. The general environmental impact of chemicals lies mainly in their ecotoxicity, which is relatively high in the case of surfactants because of their surface activity and the resulting effects on biological membranes [47]. In the case of CBS (APGs in particular), they present a quite favorable environmental profile: the rate of biodegradation is usually high, and the aquatic toxicity is low. In addition, APGs exhibit favorable dermatological properties, being very mild when exposed to the skin and eye [53]. The interested reader can find excellent overviews on APGs elsewhere [45, 46, 47, 51, 54].
Saenger and Mullerfahrnow [55] and Casu et al. [56] were pioneers in the study of the interactions between APGs and CDs. By surface tension measurements, it was shown that the addition of CDs leads to an increase of surfactant critical micelle concentration. Furthermore, the interaction is most pronounced when the CD cavity and hydrophobic part of the surfactant exhibit the tightest fit. Such a view was also supported by 1H and 13C NMR spectroscopy. By the analysis of NMR chemical shifts of octyl- (C8G1) and dodecyl (C12G1) α- and β-
α-CD | β-CD | Obs. | |
---|---|---|---|
β-C8G1 | 3.68 (±1.6) × 103 | 0.99 (±0.17) × 103 | Self-diffusion NMR [58] |
1.85 (±0.35) × 103 | Surface tension [60] | ||
β-C9G1 | 76 (±750) × 103 | 275 (±5300) × 103 | Self-diffusion NMR [58] |
β-C10G1 | 340 ± 30 | [CD] = 1 mM, 1H NMR [59] | |
β-C12G1 | 440 ± 40 | [CD] = 2 mM, 1H NMR [59] | |
410 ± 40 | [CD] = 1 mM, 1H NMR [59] | ||
β-C12G2 | 125 ± 10 | [CD] = 1 mM, 1H NMR [59] |
Binding constants, K1,1 in dm3 mol−1, for the inclusion complexes CD/APG.
Up to now, we have been discussing the binding process assuming a 1:1 APG/CD (α- and β-) binding stoichiometry. However, it should be stressed that from the study of the interactions between C12G1, and C18G1, and CDs, there are strong evidences for the occurrence of other species consistent with 1:2 complexes [56]. More recently, Haller and Kaatze, studying the interaction between C8G1 and α-CD by ultrasonic attenuation spectroscopy, concluded that besides 1:1 (APG/CD) complexes, the formation of 1:2 and 2:1 complexes (although in very low concentration) should not be ruled out [67].
As it must have already been understood from the previous subsections, an accurate choice of the technique to follow the host-guest association is a key issue for a reliable thermodynamic and kinetic characterization of the association process. In general, the experimental techniques can be subdivided into two different categories, labeled as I and II [68]. Methods from group I (e.g., surface tension) are measuring changes in physical properties that are proportional, in some ways, to the extent of binding, while those from group II (e.g., 1H NMR spectroscopy) rely on direct measurements of the free and bound ligand in a solution containing a known amount of the CD and guest molecule. Comments on such a division can be found in a couple of reviews (see, e.g., [69]), and it is outside of the scope of this chapter. The same is valid for computational techniques as relevant tools to infer on the structure of the supramolecular compounds [70, 71, 72].
In this section, the most relevant techniques used to study the interactions between CDs and sugar-based surfactants (e.g., APGs) and phytochemicals (e.g., polyphenols, EOs, and their components) will be highlighted (Table 2).
Experimental methods | System | Obs. |
---|---|---|
NMR | Nerolidol + β-CD | [74] |
UV-vis | Nerolidol + CDs1 | [74] |
Phase solubility studies | Cabreuva essential oil + HP-β-CD | [74] |
Phase solubility studies | β-caryophyllene + HP-β-CD | [76] |
UV-vis | Black pepper essential oil + HP-β-CD | [76] |
Phase solubility studies | CDs1 + PPs2 | [77] |
Phase solubility studies, NMR, TGA, DSC | β-CD + estragole | [78] |
NMR | β-CD + eugenol | [27] |
NMR | β-CD + rosmarinic acid | [75] |
NMR | Cyclohexylacetic acid + β-CD | [79] |
NMR | Cholic acid + β-CD | [79] |
UV-vis, NMR | Thymol and carvacrol + CDs1 | [80] |
NMR | n-Octyl-β- | [58] |
UAS3 | Octyl-β- | [67] |
Surface tension, NMR | APGs4 + β-CD | [59] |
Surface tension | Octyl-β- | [60] |
Phase solubility studies, ITC, NMR | Nootkatone + β-CD and HP-β-CD | [71] |
TGA | Cinnamon essential oil + β-CD | [90] |
NMR, FTIR, release kinetics | Monochlorotriazinyl β-CD + EOs5 | [91] |
XRD, NMR, TGA | Thymol + γ-CD | [30] |
DSC, TGA, FTIR, XRD, GC/MS, NMR | Isopulegol + α-CD and β-CD | [72] |
Phase solubility studies, NMR, HPLC | Polymethoxyflavones + HP-β-CD | [93] |
GC, total organic carbon, phase-solubility studies | SBE-β-CD, SBE-γ-CD and HP-β-CD + EOS6 | [94, 95] |
Compilation of the most relevant techniques used to study the interactions between CDs and bio-based compounds.
CDs: alpha-cyclodextrin (α-CD), beta-cyclodextrin (β-CD), gamma-cyclodextrin (γ-CD), 2-hydroxypropyl-β-cyclodextrin (HP-β-CD), randomly methylated-beta-cyclodextrins (RAMEB), low methylated beta-cyclodextrin (CRYSMEB), and sulfobutylether β-cyclodextrin (SBE-β-CD)
PPs: trans-anethole, estragole, eugenol, isoeugenol (phenylpropenes), caffeic acid, p-coumaric acid, and ferulic acid (hydroxycinnamic acids)
UAS: ultrasonic attenuation spectroscopy
APGs: glucopyranosides (octyl G8, decyl G10, dodecyl G12, tetradecyl G14) and two maltosides (decyl M10, dodecyl M12)
EOs: essential oils of cedarwood, clove, eucalyptus, and peppermint
EOS: essential oils of Artemisia dracunculus, Citrus reticulata Blanco, Citrus aurantifolia, Melaleuca alternifolia, Melaleuca quinquenervia, and Rosmarinus officinalis cineoliferum
NMR spectrometry falls in the group II techniques, and it is used to determine association constants through the chemical shift changes noticed either by the guest or by the CD [73, 74, 75]. Focusing on EOs, and as previously discussed, they may present undesired features, such as volatility, poor aqueous solubility, and stability. Therefore, host-guest supramolecular complexes are often obtained by using solid-state-based methods [14] such as freeze-drying [76, 77], coprecipitation [78], and the saturated approach [27], improving the solubility of the EO and thus allowing the use of NMR techniques for the quantitative and qualitative assessment of the complexation process [74]. For example, the complexation of eugenol with β-CD was obtained by using the saturation method, and the obtained complex, in the solid state, was characterized by either 1H, 13C, or 2D NMR techniques, confirming the thread of CD’s cavity by the aromatic ring of the eugenol [27]. Other techniques will be mentioned later since they fall on the so-called group II.
DOSY 1H NMR has been used to study inclusion complexes between CD and different sugar-based substrates [79]. Kfoury et al. report a comprehensive study on the complexation between two phenol isomers (thymol and carvacrol) and CDs by using different NMR techniques, including DOSY [80]. The data allowed concluding that those isomers have a binding constant of 1344 M−1 and 1336 M−1, respectively.
The self-diffusion measurements are, in principle, applicable to any systems as long as the free and complexed guests are soluble to an extent that allows for a good signal-to-noise ratio. It is important to note that on account of the rapid exchange on the NMR time scale, average diffusion coefficients for both the guest and for the CD are typically obtained. This method, as well as that involving chemical shift changes analysis, is also limited to systems where no overlapping of well-defined resonances is observed. The method relies on the fact that the self-diffusion coefficients of the uncomplexed guest are higher than the self-diffusion of the host-guest complex, as defined by the Stokes-Einstein equation. The change in the self-diffusion coefficient of the CD upon complexation is often small since the complex is often of the same size as the CD molecule, and thus the information from the CD self-diffusion is rather limited [58].
Ultrasonic relaxation technique falls into group II techniques and is based on the application of ultrasound to a given solution, with a frequency ranging from 20 kHz to several GHz, and subsequently measuring the molecular structural relaxation. The relaxation is sensitive to molecular volume changes [81], and thus, it may convey information on the stability constants of the host-guest complexes [82]. Furthermore, the use of a large frequency range allows to follow processes with relaxation times in the range from 20 ps to 20 μs [83], and thus the kinetics of the CD-surfactant association can be investigated. Haller and Kaatze, by using ultrasonic attenuation spectroscopy, were able to quantify the dynamics of unimer-micelle exchange of a sugar-based surfactant (i.e., octyl-β-
Also from group II, surface tension has also been used to follow the effect of CDs on the aggregation and interfacial properties of surfactants in CD-surfactant-containing solutions [59, 60]. Surface tension is a measure of cohesive forces between liquid molecules present at the surface, and it represents the quantification of force per unit length of free energy per unit area [84]. In general, the presence of CDs will increase the surface tension of an APG solution. Knowing that natural CDs are not surface-active, they cannot replace APG at the air interface [85]. Therefore, CD molecules contribute for the depletion of APG unimers from the interface due to the great interaction between these unimers and CDs. There are several examples where surface tension measurements have been used to assess the stoichiometry and stability constants of host-guest complexes [60, 86].
Isothermal titration calorimetry (ITC) is a sensitive and powerful technique to study host-guest interactions by measuring the enthalpy and the free energy of binding [86, 87]. There are also some cases where the kinetic constants of the binding process can be obtained by ITC (see, e.g., [88]). For example, the heat produced by a stepwise addition of HP-β- and β-CD solution to a nootkatone allowed to characterize the complexation process with a binding enthalpy and binding constant of −6.99 kJmol−1 and 4838 M−1, and −14.38 kJmol−1, and 5801 M−1, respectively [71]. Unfortunately, the strict conditions required by this technique do not allow its routine implementation on a large scale [89].
As has been pointed out before, some phytochemicals (EOs, in particular) are, in general, poorly soluble in aqueous solutions; therefore, the formation of complexes with CD in solid state is a strategy for further applications. Consequently, there are several available techniques used to evaluate the complexation. Thermal techniques, such as thermal degradation analysis and differential scanning calorimetry, are classical examples of methods used to assess complexation. Moreover, thermal degradation also allows evaluating the thermal stability of the EO upon complexation [90, 78].
Other spectroscopic techniques, such as FTIR and XRD, which can be included in group II, have also been used, but the information is, in our opinion, rather qualitative [30, 72, 78, 91]. Another interesting approach to learn about the formation of host-guest complexes, in solid state, is to study the release kinetics of the EO. These studies, although do not allow to quantify the total amount of EO incorporated into the CDs, are of utmost importance to evaluate the presence of the EO in the complex as well as to provide hints on the release mechanism; the latter is quite relevant for EOs used as fragrances [91, 92].
For such poor soluble compounds, the complexation can also be evaluated by carrying out phase-solubility studies. These can be performed by using complexes in solid state or by checking the ability of increasing concentrations of CD to solubilize saturated solutions of EO. This allows assessing how much the solubility of the EO is improved upon complexation as well as the corresponding complex binding constant. The details on the quantitative determination of those parameters will be given in the next section. Different techniques can be applied to obtain the phase-solubility profiles. For instance, the solubility of black pepper EO in the presence of hydroxypropyl-beta-CD (HP-β-CD) was evaluated by UV-visible spectroscopy [76]. On the other hand, phase-solubility profiles for the encapsulation of polymethoxyflavones, obtained from mandarin EO, into HP-β-CD were obtained by using HPLC [93]. Kfoury et al. have used gas chromatography to study the ability of sulfobutylether-β- and sulfobutylether-γ-CD to encapsulate EOs components, such as limonene, estragole, and α- and β-pinene; their solubility in water was improved more than one order of magnitude [94]. It is worth noticing that, recently, a technique based on the total organic carbon determination has been reported and validated to follow the solubility improvement of EOs when increasing the concentration of CD [95].
In this section a rather simple and straight overview of the most used model equations to compute binding constants for host-guest association is provided. To do so, EO will be used as the guest compound.
As discussed before, the phase-solubility plots are a widely applied method to get knowhow on the improvement of the EO solubility driven by complexation and also for computation of the EO-CD association constant. Assuming that the most common type of EO/CD complex has a 1:1 stoichiometry, the corresponding reaction and equilibrium (binding) constant, K1, can be written as
where G represents the guest (here the EO) and [CD]f and [G]f are the concentrations of uncomplexed (free) species in the system. Assuming that the change in the aqueous solubility of the EO (ΔS) is only due to the formation of the complex, we can write
where ST is the measurable total solubility and S0 is the solubility of the EO in water in the absence of CD (i.e., the intrinsic solubility). Thus, it follows that
where [CD]T is the total concentration of CD in the solution.
Substituting Eqs. (3)–(5) in Eq. (2) and after algebraic manipulation, we obtain
Fitting Eq. (6) to experimental data of ST = f([CD]T) allows the calculation of the intercept (S0) and the association constant, K1. As discussed by Loftsson et al., the determination of K is highly dependent on the intercept accuracy [96]. In order to overcome this drawback, the authors have established the concept of “complexation efficiency” (CE) which can be obtained independently of S0, according to the following relation:
where the term ((ST − S0)/[CD]T) represents the slope of the phase-solubility profile.
The application of Eq. (7) is useful but limited by the dependence on S0 and to 1:1 complexes.
Let us now assume the following reaction:
where n is a stoichiometry coefficient and Kn is the corresponding binding constant. Thus, from the conservation of mass equations:
and
the binding constant equation can be written as
By measuring a physical parameter, known as ΔA, directly related with the formation of the complex (CDn − G), and performing the experiment in such a way that [CD]T> > [CD − G], Eq. (11) takes the form of the so-called “Benesi-Hildebrand” equation [97]:
or its linear form
However, it should be pointed out that nowadays, with the available software, such as Origin® and MatLab®, there is no need to linearize Eq. (12) once such methodology brings some restrictions to the computation of K and n.
It should be stressed that a key point in all these procedures is the accurate previous knowledge of the stoichiometry of complexation, but this is not always a simple task. The most common method for the determination of stoichiometry is the method of continuous variation or the Job plot; the virtues and limitations of this method were recently reviewed [98], and thus it is not our intention to further discuss it in the present chapter.
Going back to the determination of the binding constants, the most accurate way to compute K is by using the first principles. Here, for the sake of simplicity, the 1:1 and 1:2 (G/CD) stoichiometric ratios will be focused. Additionally, these examples also correspond to the large majority of complexes formed between CDs and EOs. For more complex stoichiometries, the computational treatment of the resulting equations (not shown) is not straightforward as a consequence of multicollinearity [99]. Multicollinearity causes larger standard errors in the quantities calculated and lowers statistical significance of the results. In limiting cases, several local minima may be obtained by iteration; these correspond to noticeably different combinations of the quantities calculated and may be the reason why different K values are reported for the same host-guest systems.
Assuming that a 1:1 complex (CD-S) is formed, the binding constant (Eq. (2)) can be rewritten as
where f is defined as [CD − G]/[G]T.
Despite the binding process being followed by ΔA (e.g., for 1H NMR, ΔA will be equal to the chemical shift of a given 1H resonance), the observed ΔA for a host molecule is expressed as
where
The variation of the physical parameter in the presence and absence of a guest molecule, ΔAobs = ΔAobs − ΔACD, can be expressed as
which, after some algebraic manipulation and simplification, results in [100, 101]:
It should be stressed that the application of Eq. (17) shows some drawbacks when the total concentrations of CD and guest are low and/or the binding constant is very weak, i.e., for the simplest 1:1 case, when y is sufficiently small,
where
Another approach lays on the assumption of a 2:1 (CD/G) complexation, in a two-step mechanism. In these circumstances, the complexation process is defined by two binding constants K1 and K2, and the corresponding mass balances are defined as
and
From the equilibrium constants and Eqs. (19) and (20), we can write
where ACD, ACD−G, and ACD2−G are the contributions of the CD and 1:1 and 2:1 CD/G complexes, with concentrations [CD], [CD − G], and [CD2 − G], respectively, for the observed (experimental) physical parameter A. Using a similar procedure to that used for a 1:1 complexation, it is possible to write Eq. (21) as a function of [CD], that is
On the other hand, the free CD concentration is given by
One method for estimation of the free CD concentration is through an analytical solution of the real solution of a third-degree equation [103]:
using a Cardin-Tartaglia formulae
where
and
Despite the huge potential of many bio-based compounds in several diverse areas, their use is still limited due to different reasons such as poor aqueous solubility, volatility, reactivity, etc. Therefore, advanced strategies have to be developed in order to minimize some of these weaknesses to make bio-based molecules usable on a larger scale. It became patent in this chapter that CD interaction with bio-based compounds, such as different phytochemicals or sugar-based surfactants, has generally a remarkable positive impact on their performance, improving their aqueous solubility and availability and decreasing their degradation rate, etc. Moreover, it is clear that this is not only interesting and beneficial from an application point of view but also very stimulating from a fundamental perspective where thermodynamics, modeling, and different experimental methodologies get together for a deep and challenging characterization of the systems. Eventually, such knowledge will be crucial for the future development of improved formulations and make use at full extent of the exciting properties of bio-based compounds.
The Portuguese Foundation for Science and Technology (FCT) is acknowledged through the projects PTDC/AGR-TEC/4814/2014, UID/QUI/UI0313/2013, and POCI-01-0145-FEDER-07630. FCT is also acknowledged through the researcher grants IF/01005/2014, SFRH/BPD/103086/2014, and SFRH/BPD/84112/2012 financed by POPH-QREN and subsidized by the European Science Foundation.
The discovery of the giant magneto-resistance (GMR) effect in metallic multilayers by Albert Fert and Peter Grunberg has probably made a great step toward spintronics [1, 2]. To further extend applications of spintronics, researchers and engineers invent new architectures and structures, allowing to realize the integration of magnetic materials into semiconductors. The development of active spin devices, such as spin transistors or diodes, calls for new materials, which enable to efficiently inject spin-polarized currents into standard semiconductors. Two main ways have been explored in order to inject spin-polarized current into semiconductors.
Firstly, one can make use of the properties of a ferromagnetic metal (FM) such as Co, Fe, Ni, or their alloys. Spin-polarized currents tunnel from ferromagnetic metal to semiconductor through an insulator [3, 4] or a Schottky barrier [5]. However, the efficiency of spin injection directly into Si or Ge remains very low. Indeed, most of the ferromagnetic metals react with Si and Ge, leading to the formation of interfacial silicides or germanides, which, for most of them, are not ferromagnetic. It is also not trivial to obtain epitaxial growth of an oxide in between Ge (or Si) and a ferromagnetic metal; spin injection is therefore limited by the interface roughness [6].
Secondly, diluted magnetic semiconductors (DMSs), obtained by doping standard semiconductors with magnetic impurities, such as Mn or Co, have emerged as potential candidates for spin injection. The materials become ferromagnetic while conserving their semiconducting properties. They exhibit therefore natural impedance match to host semiconductors and are expected to efficiently inject spin-polarized currents into semiconductors. Since the spintronic devices often operate at room temperature and they are heated up during the operation, the great challenge and ultimate goal of the research in this field is to obtain DMSs exhibiting ferromagnetism well above room temperature. This feature represents key issues for the development of spintronic devices.
In the 1990s, DMSs of III-V-based compound semiconductors were successfully fabricated by introducing Mn ions, but Mn atoms are much less soluble than in II-VI semiconductors, making them difficult to be diluted in the III-V semiconductor, such as (GaMn)As. By using a low-temperature MBE technique, it is possible to grow thin films with higher Mn concentrations in a nonequilibrium process and prevent Mn ions to form precipitations. The TC, achieved at that time, was 110 K for 5.5% Mn-doped GaAs [7]. So far, the GaMnAs diluted magnetic semiconductors seem to be the most important and the best understood system up to now. However, they are ferromagnetic only at temperatures well below room temperature, the highest value reported was 173 K by Gallagher’s group in UK [8]. An interesting alternative could be magnetic semiconductors that are based on elemental semiconductors and also owe to their compatibility with Si microelectronics. In the last decades, considerable amount of work has been devoted to the synthesis of Mn-doped Ge and Si, such as SiMn, GeMn, and SiGeMn. The main motivations for the synthesis of these materials are:
Compatibility with mainstream silicon technology.
Mn magnetic impurity acts as an acceptor in the substitutional sites in the crystal lattice.
Very long spin relaxation time, which comes from weak spin-orbital coupling in Si and Ge [9]. It is worth noting that the spin relaxation time in IV-IV semiconductors is much larger than that in III-V semiconductors.
Although silicon is the key material of microelectronics, the first demonstration of spin injection was only achieved in 2007. Until now, it is unclear whether Mn can substitute Si sites since Mn ions in Si are fast interstitial diffusers even at low temperatures. Experimentally, numerous groups have reported the observation of ferromagnetism in Mn-doped Si with Curie temperatures ranging from 200 to 400 K [10, 11, 12, 13]. However, the origin of the observed ferromagnetism remains very diverse, which makes Mn-doped Si DMSs difficult to be realized.
Recently, special attention both in experiment and theory has been given to group-IV Ge1 − xMnx diluted magnetic semiconductors due to their compatibility with mainstream Si-based electronics. Zwicker et al. conducted the first study on the Ge-Mn equilibrium phase in the early 1949 [14]. Later on followed extensive investigations establishing the relative phase diagram [15]. The interests in GeMn system as a promising high-TC ferromagnetic semiconductor essentially started in 2002 with the publication by Park et al. [16], claiming the fabrication of a GeMn DMS with a TC up to 116 K and linear dependence on the Mn concentration. Since then, many publications investigated different aspects of the GeMn system and employed different fabrication techniques [17, 18, 19].
Despite numerous researches carried out up to now, the fabrication of homogeneous and high-TC Ge1 − xMnx films remains a challenge. It is now commonly believed that secondary phases form once the Mn concentration exceeds the solubility limit [20]. In general, when the Mn concentration and the growth temperature are high enough or after post-annealing, parasitical metallic nanoclusters of Mn5Ge3 are observed in GeMn films [21, 22, 23]. Mn11Ge8 precipitates are observed under certain conditions [24]. A result of particular interest is the discovery of the CEA group on the formation of a nanocolumn phase, which exhibits a Curie temperature higher than 400 K [25]. The nanocolumns have an average size of 5 nm and are separated from each other by a distance of about 8 nm. This phase has been attributed to a new compound, Ge2Mn, which does not exist in the Ge-Mn phase diagram.
Among numerous phases of GeMn DMS, the nanocolumns’ phase appears to be the most interesting, because it is the unique phase that has Tc higher than RT. But concerning the GeMn nanocolumns, there are some remaining questions about the composition and the mechanism of nanocolumn formation. One of the main objectives of this chapter consists of understanding the origin of the formation of this nanocolumn phase. Our purposes are to determine the nanocolumn size, driving force for self-assembly, and growth mechanisms of GeMn nanocolumns.
After the first report of ferromagnetism in the Ge1 − xMnx system with TC = ~116 K [16], the synthesis of Ge1 − xMnx DMSs has been the subject of numerous investigations [26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36]. Since it has been shown in Ref. 10 that magnetic ordering in Ge1 − xMnx linearly increases with increasing Mn concentration, a number of works have focused on investigations of the dependence of the Curie temperature of GeMn DMS on the growth parameters. Among numerous growth parameters, which can affect the Ge1 − xMnx growth behavior, the growth temperature and the Mn concentration appear to be the most important. Before presenting our results, we summarize below some major results, reporting on the influence of these two parameters on the growth and magnetic properties of GeMn DMSs.
Similar to the case of Mn in III-V semiconductors, the solid solubility of Mn in Ge is as low as 1015 cm−3 under equilibrium conditions [37]. As a consequence of such a low solubility, thin film growers use low-temperature growth to bring the system to high nonequilibrium conditions with the hope to increase the Mn concentration that can be incorporated in the films. Low-temperature growth is also expected to minimize phase separation and/or the formation of unwanted compounds. However, it is worth noting that low-temperature growth often conducts to the formation of metastable state and low crystalline quality of epilayers due to a low surface diffusion coefficient of adatoms on surface. Moreover, the ratio between interstitial and substitutional dopants may be reduced due to a too low growth temperature.
Several reports have shown that a concentration of holes up to 1017–1020 cm−3 can be obtained when doping Mn in Ge [16, 25, 29, 30, 38, 39]. It has also been demonstrated that when Mn atoms substitute Ge sites, Mn ions are in 2+ ionic states [35, 36, 40, 41]. Li et al. [38] reported on Mn ionic implantation in Ge and suggested that up to 20–30% Mn ions could be incorporated in substitutional sites and post-annealing allowed increasing this fraction to 40–50%. Some interstitial Mn ions can be converted to substitutional Mn under adequate post-annealing.
In general, it is now generally accepted by the scientific community working on GeMn DMSs that a Mn concentration up to 5–9% can be incorporated in Ge layers without creating visible metallic clusters or precipitates, such as Mn5Ge3 and Mn11Ge8. However, other kinds of Mn-rich cluster phases, in particular with size being in the range of sub-nanometer, may exist [41, 42, 43]. A question, which is still under debate, concerns the exact Mn amount or concentration that really participates in producing ferromagnetic ordering in Ge1 − xMnx materials. Answering this question certainly requires nano-scaled characterization tools for both structural and magnetic properties. Another remaining question concerns the origin of ferromagnetism in Ge1 − xMnx. If the Zener model or hole-mediated ferromagnetic model, which uses thermodynamic and micro-magnetic descriptions to explain the origin of ferromagnetism in DMS materials, is generally accepted, other mechanisms, for example bound magnetic polarons, have been proposed [36]. These authors, by combining magnetic and transport characterizations of Ge1 − xMnx films doped with ~5% of Mn, provided the existence of two magnetic transitions: TC* (~112 K) and TC (~12 K) of the layers. The transition at high temperature (TC*) can be attributed to the exchange interaction between localized charge carriers and surrounding Mn ions (magnetic polarons) while the TC transition may arise from infinite-size ferromagnetic clusters due to inhomogeneous distribution of Mn dopants inside the layers.
Together with the Mn concentration, the growth temperature is recognized as one of the main parameters that governs the growth process of GeMn films. In particular, the growth temperature has a direct consequence on the nature of phase separation or clusters that are formed in the layers: nano-scaled Mn-rich regions or metallic clusters (Mn5Ge3, Mn11Ge8 or Mn5Ge2). According to previous works, three main regions of the growth temperature can be classified: (i) above 180°C, (ii) below 80°C, and (iii) intermediate temperatures in the range from 110 to 150°C.
The most “famous” or the most frequently observed Mn-Ge clusters are certainly metallic Mn5Ge3 clusters. This phase of clusters is generally observed when the growth temperature exceeds 180°C. Figure 1 shows an example in which a high density of Mn5Ge3 clusters is present in Ge1 − xMnx films, which were grown at 225°C and contained a Mn concentration of 3% [23]. Using transmission electron diffraction (TED) and magnetic characterizations, the authors have unambiguously identified that those clusters are made of the Mn5Ge3 phase. An epitaxial relationship between these clusters and Ge(001) has been determined: a majority of them are oriented with the hexagonal (0001) plane of Mn5Ge3 being aligned with the (001) plane of Ge while some others are randomly distributed in the layers (see Figure 1) (right).
TEM images of a Ge0.97Mn0.03 epilayer on a Ge wafer (left) with a magnified section (right). The arrows mark the interface between the wafer and epilayer [27].
In the low growth temperature range, Bougeard et al. [42] reported that Ge1 − xMnx films were free of intermetallic precipitates but a new kind of cluster was formed. Figure 2a shows a plan-view TEM image of a Ge1 − xMnx film grown at 60°C with Mn content of 5%. Numerous areas exhibiting slightly darker contrast are observed; these areas were found to be coherently bounded to the surrounding Ge matrix. Analyses performed with annular dark field by scanning transmission electron microscopy (STEM) on a single cluster string (Figure 2b) revealed high structural disorder around the clusters, suggesting that they have a strained shell with a core made up by amorphous Mn [32]. Continuing their investigations, the authors recently showed that when the growth temperature increased to 85–120°C, metallic Mn5Ge3 in the shape of nanometer-sized inclusions can be formed in a diluted Ge1 − xMnx matrix [45]. It is worth noting that when post-annealing was carried out on Ge1 − xMnx films grown at the temperature range of 70–120°C, new kinds of clusters, Mn11Ge8 and Mn5Ge2 can be formed near the surface region.
High-resolution plan-view STEM images of Ge0.927Mn0.073 sample grown at 60°C. Mn-rich regions with darker contrast are amorphous Mn [44].
A result of particular interest, observed in the intermediate temperature range from 110 to 150°C, is the observation by Jamet and colleagues at CEA-Grenoble of highly elongated precipitates, which are self-organized to form nanocolumns [18]. As can be seen in the cross-sectional TEM image shown in Figure 3a, nanocolumns that are elongated along the whole GeMn layer are observed. A high-resolution TEM image shown in Figure 3b indicates that nanocolumns are coherent with the surrounding matrix and they have an average size of about 3–5 nm. By using electron energy-loss spectroscopy (EELS), the authors determined an average Mn concentration in nanocolumns ranging from 32 to 37.5% and attributed to a Ge2Mn alloy, which does not exist in the Ge-Mn phase diagram.
Transmission electron micrographs of a Ge1−xMnx film grown at 130°C and containing 6% of manganese. (a) Cross section along the [110] axis; (b) High-resolution image of the interface between the Ge1−xMnx film and the Ge buffer layer; (c) Plane view micrograph performed on the same sample; (d) Mn chemical map obtained by energy-filtered transmission electron microscopy. Bright areas correspond to Mn-rich regions [39].
One of the most interesting features of this nanocolumn phase is that it exhibits magnetic ordering well above 400 K. The temperature dependence of magnetization of the corresponding sample is shown in Figure 3a of Ref. [25]. Magnetization of the layer persists at a temperature of 400 K, the upper limit of the instrument for magnetic measurements. Shown in the insert is the M(T) measurement after subtracting the magnetic signal of nanocolumns, much lower magnetic ordering is observed and has been attributed to a Mn-poor matrix between nanocolumns. It is worth noting that the above nanocolumns were shown to be stable up to 400°C and transformed into Mn5Ge3 clusters after 15 min of annealing at 650°C. This feature represents as a starting point of our research; our purpose consists of seeking the ways to stabilize this high-TC nanocolumn phase.
The solubility limit of Mn in Ge is very low (estimated to be 1015 cm−3 [37], corresponding to a Mn atomic concentration of ≈ 2×10−6 %). While using nonequilibrium growth techniques such as low-temperature MBE growth, a much higher Mn solubility has been demonstrated. However, such a low thermodynamical Mn solubility constitutes as the main obstacle to get homogeneous highly doped GeMn films. On the other hand, the Mn dilution in a germanium crystal remains highly questionable and in most of experiments reported up to now; GeMn films are in general found to contain either nanoscaled Mn-rich regions or secondary-phase precipitates like Mn5Ge3. This means that it is crucial to combine nanoscale characterizations of the structural properties with magnetic properties in order get an accurate physical picture of grown films. The ultimate goal of research in GeMn materials could be thus find out growth techniques and growth conditions to obtain homogenous materials containing a few percent of Mn, allowing to raise the Curie temperature well above room temperature for the realization of spintronic devices. Up to now, low-temperature MBE technique has been intensively used to synthesize GeMn DMSs and promising results have been obtained [32, 33, 44, 46, 47, 48].
In our works, GeMn film growth was performed using solid source molecular beam epitaxy (MBE) on epi-ready Ge(001) wafers with a base pressure better than 1 × 10−10 Torr. Ge and Mn were evaporated using standard Knudsen effusion cells. The deposition chamber is equipped with RHEED to control the sample surface and to monitor the epitaxial growth process. The Ge deposition rate was estimated from RHEED intensity oscillations of the Ge-on-Ge homoepitaxy, whereas the Mn concentrations were deduced from Rutherford backscattering spectrometry (RBS) measurements. The cleaning of the Ge surfaces was carried out in two steps: the first was a chemical cleaning to eliminate hydrocarbon contaminants. Then, the Ge native oxide layers were etched in a diluted hydrofluoric acid solution (10%) for some minutes until a hydrophobic surface was obtained. The second step was an in situ thermal desorption of the surface oxide, which consists of outgassing the sample for several hours at 450°C followed by flash annealing at 750°C. After this step, a 40-nm-thick Ge buffer layer was grown at 250°C to ensure a good starting surface. Regarding the previous results, 80-nm-thick Ge1 − xMnx films were subsequently grown at the substrate temperature of 130°C and Mn concentrations of ~6% to ensure the reproduction of GeMn nanocolumns.
Structural analyses of the grown films were performed through extensive high-resolution transmission electron microscopy (HR-TEM) by using a JEOL 3010 microscope operating at 300 kV with a spatial resolution of 1.7 Å. Imaging at this resolution requires TEM samples to be very thin in the region of interest. As a minimum requirement, samples must be electron transparent. To take advantage of a TEM’s high resolution, it is necessary to prepare high-quality electron transparent samples. In practice, TEM specimens should be no thicker than 100 nm for low-resolution imaging and even thinner (~50 nm) for high-resolution imaging [49]. Sample preparation was carried out by standard mechanical polishing and argon ion milling. At first, the samples were cut in in two rectangular pieces (about 2 × 3 mm) and the film sides glued together with epoxy. Then, the samples were polished to a thickness of approximately 20 μm with a series of progressively smoother diamond papers. Gatan PIPS™ (Precision Ion Polishing System) ion mill was used for final thinning to electron transparency.
The surface signal of nanocolumn phase is extremely important because this allows us to know if the nucleation of the nanocolumn phase takes place. Figure 4 displays the evolution of RHEED patterns taken along the [1-10] azimuth of Ge surface during the growth of Ge0.94Mn0.06 film. Starting from RHEED pattern of the Ge surface prior to growth in Figure 4a, the Ge surface is characterized by a well-developed Ge reconstruction (2 × 1) streaky pattern, indicating that the surface is clean and smooth. This is also confirmed by the observation of high-intensity Kikuchi lines, which overlap 1 × 1 and specular streaks, giving rise to localized reinforcements of intensity. The calculations of density functional theory (DFT) are in good agreement with these results and demonstrate that in the case of the clean surface Ge (001), the total energies are minimal for this type of symmetry [50]. The Ge reconstruction streak (2 × 1) disappears after a few monolayers of GeMn co-deposition (Figure 4b), then reappears in Figure 4c. The high-intensity spots due to the diffraction in transmission begin to appear on the 1 × 1 streaks after the deposition of a few nanometers and remain present until the end of the deposition (Figure 4c and d). This indicates the formation of a new GeMn phase having the same crystal structure as that of the Ge substrate. In addition, the surface of this new phase is rough. These three-dimensional (3D) spots come from the contribution of the nanocolumns that are formed in a diluted GeMn matrix whose structure is similar to that of Ge. Indeed, during homoepitaxy of Ge on Ge at this same growth temperature, the RHEED pattern presents diffraction streaks characteristic of two-dimensional growth. The observation this type of pattern is very interesting because it indicates that the growth surface is rough and that the degree of roughness remains constant during the deposition. In other words, the vertical growth speed of the area between the nanocolumns and that of the nanocolumns themselves are almost the same because the diffraction diagram remains unchanged. In addition, by comparing with the TEM images obtained, it is pointed out that the diameter of nanocolumns is smaller than the coherence length of the incident electron beam (10 nm), which makes it possible to attribute unambiguously the 3D spots on the 1 × 1 streaks of surface diffraction to the presence of the nanocolumn phase.
RHEED patterns taken along the [1-10] azimuth of the clean Ge surface prior to growth (a), during the growth of the first monolayers (b), after 3 minutes of the growth (c), and finishing the growth process of ~80 nm Ge1 − xMnx film (d), with Mn concentration ~ 6%.
In short, in case of nanocolumn formation, the surface still exhibits a two-dimensional growth behavior although some intensity reinforcements at the Bragg diffraction positions are visible and the intensity of reconstructed ½ streaks becomes weaker—the sign of GeMn nanocolumn formation of [51]. The 3D spots situated on the 1 × 1 streaks are the contribution of Mn-rich nanocolumns formed in the diluted GeMn matrix.
Figure 5 displays typical cross-sectional TEM images of a sample grown at 130°C and with Mn content of ~6%. Dark contrast corresponds to Mn-rich regions while regions with a brighter contrast arise from the diluted matrix. The corresponding film thickness is ~80 nm. According to an overall view of the layer structure, shown in low-scaled images in Figure 5(a), we can see that the GeMn nanocolumns observed are very similar to those reported in Ref. 19. The self-assembled nanocolumns extend through the whole thickness of the GeMn layer. Most of nanocolumns are oriented perpendicular to the interface, that is, along the [001] direction. High-resolution TEM image taken around the nanocolumn inside the layer in Figure 5(b) reveals that nanocolumns are epitaxial and perfectly coherent with the surrounding diluted lattice. No defects nor presence of MnGe clusters are visible. Figure 5(c) shows that the interface is almost invisible and GeMn film exhibits the same diamond structure as Ge buffer layer. According to our previous study, at the growth temperature of Mn concentration of 6%, the nanocolumn can reach the maximum length of 80 nm before transforming into Mn5Ge3 clusters [52, 53, 54].
Typical cross-sectional TEM image of a 80-n-thick Ge1 − xMnx film with x ~ 0.06 (a), high-resolution TEM image taken inside the film (b) and around the interface region (c).
To investigate the arrangement and the size of GeMn nanocolumns, Figure 6 displays the overall and high-resolution plan-view TEM images of 80-nm-thick Ge0.94Mn0.06 film. The nanocolumns are distributed evenly on the entire film surface with the diameter of about 5–8 nm. The inter-distance between adjacent columns is about 8–10 nm. The circle shape of Mn-rich nanocolumns in plan-view TEM images means that the GeMn nanocolumns exhibit cylindrical shape. Around each column in Figure 6b, a dark ring reveals a large strain extending over a few interatomic distances. The presence of a disordered core in the columns can reveal a plastic relaxation of the misfit stress with the surrounding matrix, probably due to the high-energy electron beam of the microscope. Studying the influence of Mn content on the formation of GeMn nanocolumns, previous studies show that increasing the Mn content leads to the column density remaining nearly constant, whereas their width increases and their height decreases drastically [39, 53].
Typical (a) and high-resolution (b) plan-view TEM image of a 80-nm-thick Ge1 − xMnx film with x ~ 0.06.
In summary, GeMn nanocolumns are found to be formed at the Mn concentration of ~6%. We are thus able to stabilize the nanocolumn phase, which extends through the whole 80-nm thickness of the GeMn layer and exhibits the diamond structure elongated along the growth direction, with the diameter of about 5–8 nm.
The incorporation of impurities in a crystal lattice generally induces a constraint either at the local scale or in the whole lattice. With a very small amount of Mn (~6%), large-scale deformation is not expected. Since the atomic radius of an Mn atom (140 pm) is larger than that of a Ge atom (125 pm), the Mn-rich region, such as nanocolumns, should be in compression because of the presence of the Ge matrix surrounding them. The RHEED technique is very local but is not sufficient to be able to observe an infinitesimal constraint induced by nanocolumns. A Fourier transform of the cross-section TEM image inside the GeMn nanocolumn layers displayed in Figure 7 shows that no dislocation can be observed in the filtered image along the Bragg’s spots (220) of the red square area. This result indicates that the nanocolumn is in a stressed state. Note that filtering by the Fourier transform of the entire nanocolumn does not reveal any dislocation. It means that the nanocolumns are coherently strained in compression by the matrix along the growth direction. In any case, the presence of stress is inevitable even if the quantity of Mn incorporated is extremely small. The stress can be the important effect in the distribution of Mn atoms in the Ge matrix. A detailed study of the constraints would make it possible to better understand the mechanism of incorporation of Mn into nanocolumns and therefore to better understand the formation and growth kinetics of nanocolumns.
High-resolution cross-section TEM image of the nanocolumns (a) and the image filtered along the Bragg’s peak (220) of the red square area (b).
One of the central results concerning the nanocolumn formation is that the Mn concentration inside nanocolumns is not constant but increases from the interface to the film surface [55]. To understand the variation of the Mn concentration inside the Ge1 − xMnx nanocolumns, we attempt to provide a phenomenological explanation of the Ge1 − xMnx nanocolumn formation.
To investigate the mechanism leading to the formation of Ge1 − xMnx nanocolumn, we recall that under nonequilibrium growth carried out at a temperature as low as 130°C, the Ge lattice can dilute a Mn concentration of about 0.25–0.5% [56]. At the first stage of the growth, GeMn alloys with Mn concentration as high as ~6% are deposited on a Ge surface. This content far exceeds the solubility threshold of Mn atom in the Ge lattice. The excess Mn should diffuse and/or segregate along the surface to form Mn-rich regions. In other words, Mn-rich regions start to nucleate on the Ge surface even after deposition of the first monolayers and this is a direct consequence of the low solubility of Mn in the Ge lattice. The formation of these Mn-rich regions on the surface should “disturb” the surface morphology. This is what we have observed from RHEED patterns in Figure 4b. Probably, the presence of Mn-rich nuclei is responsible for the change in RHEED pattern of Figure 4a to RHEED pattern of Figure 4b. Since a too high Mn concentration in a nucleus is not favorable, both from the thermodynamical and epitaxial points of view, the system should self-organize to form nuclei with a certain density. The size of nuclei and the distance between nuclei depend on the Mn diffusion length on the film surface and the substrate temperature. Schema in Figure 8 illustrates the formation of these Mn-rich nuclei on the Ge surface. During the GeMn deposition process, these nuclei may serve as seeds for the nanocolumn formation. Figure 8displays a schema illustrating the Mn accumulation on the Ge(001) surface.
The scheme of Mn accumulation on Ge(001) surface.
The increase in Mn concentration within nanocolumns could be explained by vertical segregation of Mn along the [001] direction. The energy calculations along the Ge(001) orientation using spin-polarized density functional theory (DFT) show that for Ge(100) −2 × 1 surface reconstruction, Mn diffuses via the surface interstitial site (I0 site) preferentially. Mn adatoms originating from the gas phase or from deeper layers can easily diffuse toward the interstitial sites right beneath the dimers of Ge(100) −2 × 1 surface reconstruction. Therefore, growth of Mn-doped Ge(100) DMS at low temperatures should result in a high density of interstitial Mn. As Mn atoms are buried beneath a newly deposited Ge layer, they tend to float upward via the I0 sites [44, 57]. Due to this surfactant effect of Mn atoms along the [001] direction, once Mn-rich nuclei are formed on the surface, further deposition leads to the formation of GeMn columns in which the Mn concentration continuously increases from interface to the film surface. And the cylindrical shape of nanocolumns allows them to minimize their interface energy with the surrounding diluted matrix. Figure 9 displays a schema illustrating the segregation of Mn atoms during the growth GeMn nanocolumns.
The scheme of Mn atoms segregating toward the film surface through the interstitial sites during the deposition of Ge1 − xMnx film on Ge(001) substrate.
According to our previous studies, the formation of GeMn nanocolumns and Mn5Ge3 clusters is a competing process [52]. During the growth, Mn continuously segregates toward the film surface and GeMn nanocolumns are found to transform to metallic Mn5Ge3 precipitates once the Mn concentration inside nanocolumns exceeds a highest value about 40%. It means that depending on the Mn concentration in the top of nanocolumns, nanocolumn growth can be interrupted. In the same time, other nanocolumns can start to nucleate in the middle of the layer if these regions are rich enough in Mn to form new nuclei. Figure 10 displays a schema illustrating the growth competition between Ge1 − xMnx nanocolumns and Mn5Ge3 clusters.
The scheme of growth competition between Ge1 − xMnx nanocolumns and Mn5Ge3.
Another interesting feature of nanocolumns is their core-shell structure [52, 53]. The Mn concentration across a nanocolumn is not homogenous; nanocolumns exhibit a core-shell structure with a much higher Mn concentration in the core compared to that of the shell. The Mn concentration in GeMn nanocolumns is highly inhomogeneous, it increases from interface to the film surface and also from the shell to the core of nanocolumns. Since the atomic radius of Mn atoms is slightly larger than that of Ge (127 and 122 picometers for Mn and Ge atoms, respectively), if the Mn concentration inside nanocolumns is too high, nanocolumns may exert a tensile strain on the surrounding lattice. To reduce such a strain, a core-shell structure with a reduced Mn concentration from core to shell should allow nanocolumns to more easily adapt the lattice parameter of the surrounding lattice. Thanks to this self-organized core-shell structure, almost all nanocolumns are found to be perfectly coherent with the surrounding lattice, as can be seen in Figure 5.
In conclusion, GeMn nanocolumns elongated along the growth direction are found to be formed at the growth temperature of 130°C and Mn concentration of ~6%. Based on the surface signals of GeMn nanocolumn formation, we are thus able to stabilize the nanocolumn phase, which exhibits the same diamond structure as Ge substrate with the diameter of about 5–8 nm and the maximum height of 80 nm. We have attempted to explain the nanocolumn formation using a phenomenological model based on Mn segregation and diffusion both in-plane and along the growth direction: (i) Mn-rich regions start to nucleate on the Ge surface even after deposition of the first monolayers and this is a direct consequence of the low solubility of Mn in the Ge lattice; (ii) due to the surfactant effect of Mn atoms along the [001] direction, further deposition leads to the formation of GeMn nanocolumns in which the Mn concentration continuously increases from interface to the film surface; (iii) GeMn nanocolumns become unstable when the Mn concentration reaches a value of 40% and then transform into Mn5Ge3 clusters. The shell-core structure of the column is formed to reduce strain, which is induced due to the difference in atomic radius between Ge and Mn.
The author thanks colleagues at Interdisciplinary Center of Nanoscience of Marseille (CINaM-CNRS), Aix-Marseille University, France for their technical help and fruitful discussions.
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