\r\n\tThe versatility and multifarious skills of Underwater Work mean that it’s possible to operate over a wide range of activities, working in hyperbaric conditions or in confined spaces. The experience in the field and the detailed knowledge of diving procedures also enable the divers to operate in highly specific segments: inspection of civil-engineering structures; undersea foundations and welds; ship hull inspections and raising of wrecks; work in hostile and nuclear environments; dam inspections using an ROV (Remotely Operated Vehicle); installing or commissioning outfalls, undersea conduits and cables. \r\n\t \r\n\tVirtually all the civil-engineering trades and crafts can be transposed to Underwater Work, as in the case of high-pressure cleaning, cementing, welding, cutting, etc. \r\n\t \r\n\tNowadays, mainly stimulated by the development and encouragement of underwater oil exploration, the technical means in the form of diving equipment, installations, electronic equipment, compression and decompression chambers, as well as surface support vessels, are increasingly complex and require an ever better-prepared staff. \r\n\tThe main aim of this book is to expose and discuss the inner workings of Underwater Work, its challenges and opportunities. \r\n\t \r\n\tUnderwater Work - know, recognize the unknown, explore a new world.
",isbn:"978-1-78985-229-5",printIsbn:"978-1-78985-222-6",pdfIsbn:"978-1-78985-230-1",doi:null,price:0,priceEur:0,priceUsd:0,slug:null,numberOfPages:0,isOpenForSubmission:!1,hash:"647b4270d937deae4a82f5702d1959ec",bookSignature:"Dr. Sérgio António Neves Lousada",publishedDate:null,coverURL:"https://cdn.intechopen.com/books/images_new/9280.jpg",keywords:"Control Systems, Fluid Mechanics, Ocean Engineering, Structural Mechanics, Solid Mechanics, Subaquatic Morphology, Thermodynamics, Underwater Architecture, Underwater Engineering, Applied Mechanics, Maintenance, Diving",numberOfDownloads:269,numberOfWosCitations:0,numberOfCrossrefCitations:0,numberOfDimensionsCitations:0,numberOfTotalCitations:0,isAvailableForWebshopOrdering:!0,dateEndFirstStepPublish:"September 20th 2019",dateEndSecondStepPublish:"March 2nd 2020",dateEndThirdStepPublish:"May 1st 2020",dateEndFourthStepPublish:"July 20th 2020",dateEndFifthStepPublish:"September 18th 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:"248645",title:"Dr.",name:"Sérgio António",middleName:null,surname:"Neves Lousada",slug:"sergio-antonio-neves-lousada",fullName:"Sérgio António Neves Lousada",profilePictureURL:"https://mts.intechopen.com/storage/users/248645/images/system/248645.jpeg",biography:"Sérgio António Neves Lousada is a Civil Engineer with a PhD\nin civil engineering and his area of knowledge is in hydraulics.\nHe teaches at the University of Madeira, Faculty of Exact Sciences and Engineering, in the Civil Engineering course, with a\nmajor field of hydraulics, environment and water resources and\nsecondary field of construction. Currently he is course director\nof the First Cycle in Civil Engineering, according to the statement of the Scientific Council of the Faculty of Exact Sciences and Engineering at\nthe University of Madeira. Since 2012, he has been researching hydraulic sciences,\nparticularly in the areas of hydraulics, urban hydraulics and marine and fluvial construction. He has published several articles and books and has participated in events\nmainly in the areas of hydraulics, urban planning, and land management.",institutionString:"University of Madeira",position:null,outsideEditionCount:0,totalCites:0,totalAuthoredChapters:"5",totalChapterViews:"0",totalEditedBooks:"0",institution:{name:"University of Madeira",institutionURL:null,country:{name:"Portugal"}}}],coeditorOne:null,coeditorTwo:null,coeditorThree:null,coeditorFour:null,coeditorFive:null,topics:[{id:"11",title:"Engineering",slug:"engineering"}],chapters:[{id:"74156",title:"Diving as a Scientist: Training, Recognition, Occupation - The “Science Diver” Project",slug:"diving-as-a-scientist-training-recognition-occupation-the-science-diver-project",totalDownloads:68,totalCrossrefCites:0,authors:[null]},{id:"71423",title:"Progressive Underwater Exploration with a Corridor-Based Navigation System",slug:"progressive-underwater-exploration-with-a-corridor-based-navigation-system",totalDownloads:99,totalCrossrefCites:0,authors:[{id:"152460",title:"Dr.",name:"Mario",surname:"Jordán",slug:"mario-jordan",fullName:"Mario Jordán"}]},{id:"72795",title:"Cross-Correlation-Based Fisheries Stock Assessment Technique: Utilization of Standard Deviation of Cross-Correlation Function as Estimation Parameter with Four Acoustic Sensors",slug:"cross-correlation-based-fisheries-stock-assessment-technique-utilization-of-standard-deviation-of-cr",totalDownloads:69,totalCrossrefCites:0,authors:[null]},{id:"74726",title:"Underwater Technical Inspections Using ROV Applied to Maritime and Coastal Engineering: The Study Case of Canary Islands",slug:"underwater-technical-inspections-using-rov-applied-to-maritime-and-coastal-engineering-the-study-cas",totalDownloads:34,totalCrossrefCites:0,authors:[{id:"248645",title:"Dr.",name:"Sérgio António",surname:"Neves Lousada",slug:"sergio-antonio-neves-lousada",fullName:"Sérgio António Neves Lousada"}]}],productType:{id:"1",title:"Edited Volume",chapterContentType:"chapter",authoredCaption:"Edited by"},personalPublishingAssistant:{id:"184402",firstName:"Romina",lastName:"Rovan",middleName:null,title:"Ms.",imageUrl:"https://mts.intechopen.com/storage/users/184402/images/4747_n.jpg",email:"romina.r@intechopen.com",biography:"As an Author Service Manager my responsibilities include monitoring and facilitating all publishing activities for authors and editors. 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1. Introduction
Today, the term “functional polymers” is used to compare the specific properties such as chemical, physicochemical or biochemical functions of polymeric materials and to classify polymers in this field. For the preparation of different purpose polymers, new monomers are obtained by binding the functional group to the structure of certain monomers. Copolymers of commercial monomers and monomers with functional groups are prepared and their properties are investigated. In addition, chemical polymers are chemically modified and functional groups are bonded to produce chemical-reactive polymers in both the industry and polymer-based chemistry. The application of chemical modification to the polymers is used to prepare polymers which cannot be prepared by direct polymerization of the monomer.
There are two ways to synthesize a polymer with the planned pendant reactive group: (1) functionalization of a non-functional polymer by chemical modification; (2) binding of a reactive side group to the monomer and polymerization of this reactive group monomer by chain addition polymerization methods [1]. Both methods have been successfully applied to obtain vinyl polymers. The synthesis and studies on (meth)acrylate polymers have attracted the attention of various groups in recently [2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13]. Acrylate homopolymers along with their copolymers are used in various fields such as thin films, adsorption, fibers, filament coatings, lithography, lacquers, adhesives, printing inks, and binders [14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34].
There are some disadvantages in linking functional groups on polymers:
The distribution of bound functional groups on polymer molecules may not be regular.
The density of the bound reactive groups is generally low, and therefore, in such polymers, there may be no results in terms of reaction between the functional group and the polymer structure.
Polymer functionalization reactions should be carried out in temperate conditions and the efficiency of the reactions should be quantitative. Because it will be a part of the polymer chain in the undesirable groups that may occur by side reactions. Therefore, precautions should be taken in such a way that no side reactions occur as long as possible.
The activity of the groups to be bound on the polymer molecules may be different due to the surrounding of the macromolecule compared to similar small molecules. Therefore, more characteristic reaction conditions may be required for a satisfactory transformation.
Side reactions during the polymer functionalization reaction will produce impurities in the obtained polymer due to unreacted groups and other functional groups, which will reveal the problem of purification.
Due to undesirable side reactions, the chemical and physical properties of the polymer, such as dissolution, cross-linking, halogen and gas release, can be varied.
Since the functional groups allow for cross-linking during polymerization and the polymer will not dissolve, there may not be sufficient analytical methods to investigate the properties of the polymer.
In particular, where the polymer chain is susceptible to chemical reactions, reactions should be carried out without degradation.
2. Functional methacrylate ester monomer and polymer synthesis from oxirane compounds
2.1 Synthesis of aryloxy-2,3-epoxy propane (oxirane)
The oxirane compound is obtained from the epichlorohydrin with an arylalcohol. The synthesis reaction scheme is given in Figure 1.
Figure 1.
Reaction scheme of aryloxy-2,3-epoxy propane.
A typical procedure for the reaction of arylalcohol with epichlorohydrin is as follows: arylalcohol (0.5 mol) and epichlorohydrin (1.5 mol) and sodium hydroxide (0.55 mol) are mixed with magnetic stirrer at 50°C for 10 h, and then the reaction mixture is stirred at room temperature for 15 h. The organic layer is washed several times with diethylether and dried over magnesium sulfate. After removing diethylether, the excess of epichlorohydrin is distilled at 50°C and 60 mmHg. The remaining reaction mixture is distilled at 110°C and 12 mmHg (oxirane product yield: 87%). The structure of the compound aryloxy-2,3-epoxy propane is identified by the FT-IR techniques. FT-IR (cm−1): 3100–2800 (C▬H); 1590 (C〓C); 1250 (epoxy C▬O); 950–770 (epoxy C▬H).
2.2 Synthesis of aryloxy-2-hydroxypropyl methacrylate monomer
Oxirane compound is distilled off again at 110°C and 12 mmHg by vacuum distillation. In a reaction flask, 0.26 mol of oxirane, 0.54 mole of methacrylic acid, 0.30 mol of pyridine, and 100 ppm of hydroquinone are mixed in 200 ml of toluene solvent at 85°C for 24 h with a magnetic stirrer. After the reaction is complete, 30% sodium hydroxide solution is added until the mixture is taken up in ethereal separation funnel and basic. The basic aqueous phase obtained at the end of the extraction is extracted three times with diethylether in another separating funnel. The collected ethereal phases are taken to the separating funnel and extracted until neutral with water. The etheric phases are taken into a collection container and a sufficient amount of anhydrous magnesium sulfate is thrown into it and left to dry for 24 h. At the end of the filtration process, the mixture separated from magnesium sulfate is distilled off the toluene at 45°C and 50 mmHg. To the remaining mixture, 50 ppm of hydroquinone was added and vacuum distillation is carried out with monomer at 150°C and 1 mmHg (monomer yield: 65%). The synthesis reaction scheme is given in Figure 2.
Figure 2.
Reaction scheme of aryloxy-2-hydroxypropyl methacrylate monomer.
The structure of the monomer is confirmed by the FT-IR and 1H- and 13C-NMR spectroscopic techniques. FT-IR (cm−1): 3600–3200 (▬OH); 3100–2800 (C▬H); 1720 (>C〓O); 1630 (CH2〓C); 1580 (aromatic, C〓C); 1250 (C▬O). 1H-NMR (CDCl3, TMS): 8.0–6.8 (aromatics ▬H); 6.2–5.44 (CH2〓C); 4.25 (O▬H); 1.8 (CH3). 13C-NMR (CDCl3, TMS): 157.2–113.8 (aromatics ▬C); 134.0–124.4 (CH2〓C); 165.6 (>C〓O); 67.8 (CH▬OH); 17.2 (CH3).
2.3 Free radical polymerization of aryloxy-2-hydroxypropyl methacrylate monomer
Appropriate amounts of aryloxy-2-hydroxypropyl methacrylate monomer and chloroform and 2,2′-azobisisobutyronitrile (AIBN) as an initiator (2% of the monomer mass) are disposed in a polymerization tube and liquidated with nitrogen for 10 min. The sealed and waxed polymerization reaction tube is placed at 60 ± 1°C for 24 h in oil bath. The reaction product is poured dropwise into an abundant of diethylether. The obtained polymer is purified by re-precipitation with diethylether from a chloroform solution and the latest operation dried under vacuum oven (conversion 90%). The synthesis reaction scheme is given in Figure 3.
Figure 3.
Reaction scheme of poly aryloxy-2-hydroxypropyl methacrylate.
The formation of the homopolymer of aryloxy-2-hydroxypropyl methacrylate is confirmed by the FT-IR and 1H-NMR spectroscopic techniques. The main description for the polymerization of the monomer is that the characteristic double bond (vinyl structure double bond) peak signal of the monomer in the FT-IR spectrum is fully depleted and does not peak in this region in the FT-IR spectrum of the polymer. This is because the addition polymerization proceeds through the opening of the pi bond in the vinyl group. This has been effectively observed in the synthesis and characterizations herein. Two signals altered in the FT-IR spectrum of the monomer: the stretching vibration band of the vinyl group C〓C at 1630 cm−1 and the absorption signal at 920 cm−1 assigned to the C▬H bending of geminal〓CH2.
The information is clearly seen in 1H-NMR spectroscopy on polymer formation. The formation of polymer is clearly evident from the disappearing of the two singlets at 6.3 and 5.4 ppm of the vinyl protons and the wide peaks at 2.4–1.3 ppm due to the conversion to the aliphatic ▬CH2 group.
3. Functional methacrylate ester monomer and polymer synthesis from arylacetylhalide compounds
3.1 Synthesis of arylacetylhalide
Arylacetyl chloride is prepared by reacting arylalcohol with chloroacetyl chloride using the K2CO3. A typical procedure for the acylation reaction of arylalcohol with chloroacetyl chloride is as follows: arylalcohol (1 mol) and K2CO3 are dissolved in 20 ml of anhydrous benzene at 0°C, and then 1.1 mol of chloroacetyl-chloride is added dropwise to this solution. The reaction mixture is stirred at room temperature for 15 h. The organic layer is washed several times with diethylether and dried over MgSO4. After removing diethylether, α-chloro-arylacetamide is crystallized from methanol (yield: 80%). The structure of the compound arylacetylhalide is identified by the FT-IR techniques. FT-IR (cm−1): 3100–2800 (C▬H); 1730 (>C〓O); 1580 (aromatic, C〓C). The synthesis reaction scheme is given in Figure 4.
Figure 4.
Reaction scheme of arylacetylhalide.
3.2 Synthesis of aryloxycarbonyl methyl methacrylate monomer
Aryloxycarbonyl methyl methacrylate is synthesized as follows: a mixture of arylacetyl chloride (1 mol), sodium methacrylate (1.1 mol) in 100 ml acetonitrile and triethylbenzylammonium chloride (TEBAC) (0.1 mol) as a phase transfer catalyst better and sodium iodide (NaI) (0.1 mol) as catalyst are receipt in a three-neck round bottom flask equipped with a thermometer, magnetic stirrer, and heated to 85°C in a reflux condenser in the presence of 100 ppm hydroquinone. The reaction is continued for an additional 30 h. The reaction mixture is cooled to 20°C and moved to a separating funnel, washed sequentially with diethylether, 5% NaOH, and distilled water. The organic layer are spooled and dried over anhydrous magnesium sulfate (MgSO4) for 24 h. Magnesium sulfate is filtered and the diethylether is removed from the organic layers with a rotary evaporator. The resulting monomer is purified by recrystallization from ethanol (yield: 85%). The synthesis reaction scheme is given in Figure 5.
Figure 5.
Reaction scheme of aryloxycarbonyl methyl methacrylate monomer.
The structure of the monomer is confirmed by the FT-IR and 1H- and 13C-NMR spectroscopic techniques. FT-IR (cm−1): 3100–2800 (C▬H); 1730 (>C〓O); 1630 (CH2〓C); 1580 (aromatic, C〓C); 1250 (C▬O). 1H-NMR (CDCl3, TMS): 7.9–6.6 (aromatics ▬H); 6.2–5.41 (CH2〓C); 1.8 (CH3). 13C-NMR (CDCl3, TMS): 157.1–113.4 (aromatics ▬C); 134.4–124.2 (CH2〓C); 165.2 (>C〓O); 18.1 (CH3).
3.3 Free radical polymerization of aryloxycarbonyl methyl methacrylate monomer
Homopolymer of aryloxycarbonyl methyl methacrylate is synthesized using 2,2′-azobisisobutyronitrile (AIBN) as an initiator (2% of the monomer mass) in 1,4-dioxane solution. The reaction mixture is de-aerated by passing nitrogen gas for 10 min, then the tube is tightly sealed and kept in a thermostatic oil bath at 60 ± 1°C for 24 h. The homopolymer is precipitated in excess methanol, purified by dissolution in 1,4-dioxane and reprecipitation in methanol. The homopolymer is dried in vacuum to constant weight (conversion 90%). The synthesis reaction path is given in Figure 6.
Figure 6.
Reaction scheme of poly aryloxycarbonyl methyl methacrylate.
The formation of the homopolymer of aryloxycarbonyl methyl methacrylate is confirmed by the 1H-NMR and FT-IR spectroscopic techniques. The information is clearly seen in 1H-NMR spectroscopy on polymer formation. The formation of polymer is clearly evident from the disappearing of the two singlets at 6.3 and 5.4 ppm of the vinyl protons and the wide peaks at 2.4–1.3 ppm due to the conversion to the aliphatic-CH2 group. The main description of the polymer is exactly the extinction of some characteristic peaks of the double bond in the FT-IR spectrum, and this has been effectively observed in the synthesis and characterizations herein. Two signals altered in the FT-IR spectrum of the monomer: the stretching vibration band of the vinyl group C〓C at 1630 cm−1 and the absorption signal at 920 cm−1 assigned to the C▬H bending of geminal〓CH2.
4. Functional methacrylate ester monomer and polymer synthesis from α-chloro-N-arylacetamide compounds
4.1 Synthesis of α-chloro-N-arylacetamide
α-chloro-N-arylacetamide is prepared by reacting arylamine with chloroacetylchloride using the K2CO3. A typical procedure is as follows: arylamine (1 mol) and K2CO3 were dissolved in 20 ml of anhydrous benzene at 0°C, and then 1.1 mol of chloroacetylchloride are added dropwise to this solution. The reaction mixture is stirred at room temperature for 15 h. The organic phase is washed several times with diethylether and dried over MgSO4. After removing diethylether, α-chloro-N-arylacetamide is crystallized from methanol (yield: 80%). The synthesis reaction scheme is given in Figure 7.
Figure 7.
Reaction scheme of α-chloro-N-arylacetamide.
The structure of the compound α-chloro-N-arylacetamide is identified by the FT-IR techniques. FT-IR (cm−1): 3340 (NH); 3100–2800 (C▬H); 1680 (>C〓O); 1580 (aromatic, C〓C).
4.2 Synthesis of arylamido methyl methacrylate monomer
Arylamido methyl methacrylate is synthesized as follows: 1.1 mol sodium methacrylate, 1 mol α-chloroacetamide, 0.1 mol NaI and 0.1 mol TEBAC and as catalyst are stirred in 100 ml acetonitrile at 80°C in a reflux condenser for 30 h in the presence of 100 ppm hydroquinone. After the solution is cooled to 20°C and neutralized with a 5% NaOH solution. The organic phase is washed a few times with water, and the water phase is washed with diethylether a several times. The diethyl ether phase and the acetonitrile phase are spooled and dried over anhydrous magnesium sulfate for 24 h. Diethyl ether and acetonitrile are removed with a rotary evaporator. The organic phases are collected and the residue is distilled at 130°C at 5 mmHg to give a colorless liquid (yield: 80%). The synthesis reaction scheme is given in Figure 8.
Figure 8.
Reaction scheme of arylamido methyl methacrylate monomer.
The structure of the monomer is confirmed by the FT-IR and 1H- and 13C-NMR spectroscopic techniques. FT-IR (cm−1): 3325 (NH); 3100–2800 (C▬H); 1680 (>C〓O); 1630 (CH2〓C); 1580 (aromatic, C〓C); 1230 (C▬O▬C). 1H-NMR (CDCl3, TMS): 9.1 (N▬H); 8.0–6.7 (aromatics ▬H); 6.3–5.43 (CH2〓C); 1.8 (CH3). 13C-NMR (CDCl3, TMS): 157.1–113.4 (aromatics ▬C); 134.4–124.2 (CH2〓C); 168.1 (>C〓O); 18.1 (CH3).
4.3 Free radical polymerization of arylamido methyl methacrylate monomer
Arylamido methyl methacrylate monomer is freed from inhibitor by washing with a dilute KOH solution followed by distilled water and then drying over MgSO4. Appropriate amounts of arylamido methyl methacrylate monomer, 2,2′-azobisisobutyronitrile (AIBN) (2% of the monomer mass) and 1,4-dioxane are placed in a polymerization reaction tube and purged with nitrogen for 15 min. The closed mouth polymerization reaction tube is kept at 60 ± 1°C for 30 h in oil bath. The reaction product is poured dropwise into an abundant of n-hexane. The obtained polymer is purified by re-precipitation with n-hexane from a 1,4-dioxane solution and the latest operation dried under vacuum oven (conversion 90%). The synthesis reaction scheme is given in Figure 9.
Figure 9.
Reaction scheme of poly arylamido methyl methacrylate.
The structure of poly arylamido methyl methacrylate is confirmed by the FT-IR and 1H-NMR spectroscopic techniques. The main description for the polymerization of the monomer is that the characteristic double bond (vinyl structure double bond) peak signal of the monomer in the FT-IR spectrum is fully depleted and does not peak in this region in the FT-IR spectrum of the polymer. This is because the addition polymerization proceeds through the opening of the pi bond in the vinyl group. This has been effectively observed in the synthesis and characterizations herein. Two signals altered in the FT-IR spectrum of the monomer: the stretching vibration band of the vinyl group C〓C at 1630 cm−1 and the absorption signal at 920 cm−1 assigned to the C▬H bending of geminal〓CH2.
The information is clearly seen in 1H-NMR spectroscopy on polymer formation. The formation of polymer is clearly evident from the disappearing of the two singlets at 6.3 and 5.4 ppm of the vinyl protons and the wide peaks at 2.8–1.4 ppm due to the conversion to the aliphatic ▬CH2 group.
5. Functional methacrylate ester monomer and polymer synthesis from aryl-1,3-dioxolane compounds
5.1 Synthesis of (aryl-1,3-dioxolane-4-yl) methanol
(Aryl-1,3-dioxalan-4-yl)methanol is prepared by reacting arylaldehyde with glycerin using the p-toluenesulfonic acid as catalyst. A typical procedure is as follows: Arylaldehyde (0.1 mol), glycerin (0.1 mol), p-toluenesulfonic acid (p-TOS) (0.5 g, as catalyst) and toluene (30 mL) are placed in a 100 mL three-necked reaction balloon fitted with a thermometer, condenser and a stirrer. The reaction mixture is refluxed at 115°C for 2 h with strong mixing. The reaction mixture is extracted a few times with diethyl ether and then 5% KOH solution, diethyl ether and toluene, respectively. The diethyl ether and toluene solvents are evaporated with rotary evaporator. The raw product is washed with water (40 mL × 3) and dried over anhydrous magnesium sulfate at overnight. The synthesis reaction scheme is given in Figure 10.
Figure 10.
Reaction scheme of (aryl-1,3-dioxolane-4-yl) methanol.
The structure of (aryl-1,3-dioxolane-4-yl) methanol is identified by the FT-IR and 1H- and 13C-NMR spectroscopic techniques. FT-IR (cm−1): 3500–3110 (O▬H); 3100–2800 (C▬H); 1570 (aromatic, C〓C); 1180 (C▬O▬C). 1H-NMR (CDCl3, TMS): 7.48–7.0 (aromatics ▬H); 6.3–5.52 (CH2〓C); 4.0–3.7 (▬O▬CH); 4.17–4.11 (O▬CH2); 3.16 (▬OH), 3.0 (CH2). 13C-NMR (CDCl3, TMS): 151.1–116.4 (aromatics ▬C); 134.4–124.2 (CH2〓C); 63.1 (CH2); 68.8 (O▬CH2); 77.3 (O▬CH).
5.2 Synthesis of (aryl-1,3-dioxolane-4-yl) methyl acrylate monomer
(Aryl-1,3-dioxalan-4-yl)methanol (0.1 mol), triethyl amine (NR3) (20 mL, as catalyst) and diethyl ether (40 mL) are filled in a 250 mL four-necked reaction balloon fitted with a thermometer, a condenser, a stirrer and an addition funnel including 15 mL acryloyl chloride. The acryloyl chloride is added drop wise to the solution with a dropping funnel. The temperature of the reaction mixture is hold by a cryostat at −5°C for 18 h. The reaction mixture is extracted a few times with 5% KOH solution and after dried over anhydrous magnesium sulfate for 24 h. The solvents are removed by the vacuum evaporator. The synthesis reaction scheme is given in Figure 11.
Figure 11.
Reaction scheme of (aryl-1,3-dioxolane-4-yl) methyl acrylate monomer.
The structure of (aryl-1,3-dioxolane-4-yl) methyl acrylate is confirmed by the FT-IR and 1H- and 13C-NMR spectroscopic techniques. FT-IR (cm−1): 3100–2800 (C▬H); 1727 (>C〓O); 1630 (CH2〓C); 1570 (aromatic, C〓C); 1190 (C▬O▬C). 1H-NMR (CDCl3, TMS): 7.6–7.0 (aromatics ▬H); 6.3–5.52 (CH2〓C); 5.8 (Ar▬CH); 4.2–3.8 (▬O▬CH); 4.2–4.1 (O▬CH2); 3.0 (CH2). 13C-NMR (CDCl3, TMS): 166.2 (>C〓O); 151.1–116.4 (aromatics ▬C); 130.4–122.2 (CH2〓C); 103.2 (Ar▬CH); 63.1 (CH2); 68.8 (O▬CH2); 87.2 (O▬CH).
5.3 Free radical polymerization of arylamido methyl methacrylate monomer
Free radical polymerization reaction of (aryl-1,3-dioxolane-4-yl) methyl acrylate monomer is conducted in a polymerization reaction tube using 2,2′-azobisisobutyronitrile (AIBN) (1% of the monomer mass) as initiator in 10 mL of 1,4-dioxane, at 65°C with 90% conversion in 6 h. The formed polymer is precipitated in ethyl alcohol. The obtained polymer is dried under vacuum at 45°C for 24 h for constant weight. The synthesis reaction scheme is given in Figure 12.
Figure 12.
Reaction scheme of poly(aryl-1,3-dioxolane-4-yl) methyl acrylate.
The structure of poly(aryl-1,3-dioxolane-4-yl) methyl acrylate is confirmed by the FT-IR and 1H-NMR spectroscopic techniques. The information is clearly seen in 1H-NMR spectroscopy on polymer formation. The formation of polymer is clearly evident from the disappearing of the two singlets at 6.3 and 5.42 ppm of the vinyl protons and the wide peaks at 2.9–1.5 ppm due to the conversion to the aliphatic ▬CH2 group. The main description of the polymer is exactly the extinction of some characteristic peaks of the double bond in the FT-IR spectrum, and this has been effectively observed in the synthesis and characterizations herein. Two signals altered in the FT-IR spectrum of the monomer: the stretching vibration band of the vinyl group C〓C at 1630 cm−1 and the absorption signal at 920 cm−1 assigned to the C▬H bending of geminal〓CH2.
6. Functional methacrylate ester monomer and polymer synthesis from benzofuran compounds
6.1 Synthesis of acetyl benzofuran
Synthesis of acetyl benzofuran is as follows: Potassium carbonate (K2CO3) (0.1 mol) and 2-hydroxybenzaldehyde (1 mol) are dissolved in 30 ml of absolute acetone. The reaction mixture is taken in a three-neck round bottom reaction balloon equipped with a magnetic stirrer, a thermometer, and cooled to 0°C. After then chloroacetone (1.1 mol) are added dropwise to this solution at 5°C, and stirred at 20°C for 16 h. The organic phase is washed a few times with distilled water and separation layer is filtered through filter paper and dried over anhydrous MgSO4 overnight. Acetyl benzofuran compound is crystallized from ethyl alcohol. Yield: 85%. The synthesis reaction scheme is given in Figure 13.
Figure 13.
Reaction scheme of acetyl benzofuran.
The structure of acetyl benzofuran is identified by the FT-IR techniques. FT-IR (cm−1): 3100–2800 (C▬H); 1690 (>C〓O); 1570 (aromatic, C〓C).
6.2 Synthesis of bromo-acetyl benzofuran
Acetyl benzofuran (1 mol) is dissolved in 200 mL acetic acid, and after then bromo is added dropwise to this solution at 25°C for 2 h. After bromination reaction, the mixture is divided into ice-water. The separation layer is filtered through filter paper and dried over anhydrous magnesium sulfate (MgSO4) overnight. Bromo-acetyl benzofuran compound is crystallized from ethyl alcohol. Yield: 85%. The synthesis reaction scheme is given in Figure 14.
Figure 14.
Reaction scheme of bromo acetyl benzofuran.
The structure of bromo acetyl benzofuran is identified by the FT-IR techniques. FT-IR (cm−1): 3100–2800 (C▬H); 1690 (>C〓O); 1570 (aromatic, C〓C); 780 (CH▬Br).
6.3 Synthesis of acetyl benzofuryl methyl methacrylate monomer
Sodium methacrylate (1.1 mol), bromo-acetyl benzofuran (1 mol), sodium iodide (0.1 mol) and triethylbenzylammoniumchloride (TEBAC) (0.1 mol) as catalyst are mixed in 100 mL acetonitrile at 70°C in a reflux condenser for 20 h in the beside of 100 ppm hydroquinone as an inhibitor. After then the solution is cooled to 20°C and neutralized with a 5% NaOH solution. The organic phase is washed with diethyl ether a few times. The diethyl ether and acetonitrile layers are spooled and dried over anhydrous magnesium sulfate (MgSO4) overnight. Diethyl ether and acetonitrile are evaporated with a rotary evaporator. The organic layers are collected and the residue is crystallized from ethyl alcohol. Yield: 80%. The synthesis reaction scheme is given in Figure 15.
Figure 15.
Reaction scheme of acetyl benzofuryl methyl methacrylate monomer.
The structure of acetyl benzofuryl methyl methacrylate is confirmed by the FT-IR and 1H- and 13C-NMR spectroscopic techniques. FT-IR (cm−1): 3100–2800 (C▬H); 1735 (>C〓O); 1685 (▬C〓O); 1630 (CH2〓C); 1580 (aromatic, C〓C); 1190 (C▬O▬C). 1H-NMR (CDCl3, TMS): 7.7–7.2 (aromatics ▬H); 6.3–5.48 (CH2〓C); 4.2–4.0 (O▬CH2); 1.5 (CH3). 13C-NMR (CDCl3, TMS): 178.2 (▬C〓O); 168.1 (>C〓O); 148.1–116.2 (aromatics ▬C); 130.1–122.0 (CH2〓C); 68.8 (O▬CH2); 19.1 (CH3).
6.4 Free radical polymerization of acetyl benzofuryl methyl methacrylate monomer
The preparation of homopolymer of Acetyl benzofuryl methyl methacrylate monomer is synthesized by free radical polymerization in 1,4-dioxane solvent using 2,2′-azobisisobutyronitrile (AIBN) as a free radical initiator. The homopolymer is purified by repeated reprecipitation from 1,4-dioxane and then filtered and dried until a constant weight is attained. The synthesis reaction path is given in Figure 16.
Figure 16.
Reaction scheme of poly acetyl benzofuryl methyl methacrylate.
The structure of poly acetyl benzofuryl methyl methacrylate is confirmed by the FT-IR and 1H-NMR spectroscopic techniques. The information is clearly seen in 1H-NMR spectroscopy on polymer formation. The formation of polymer is clearly evident from the disappearing of the two singlets at 6.3 and 5.42 ppm of the vinyl protons and the wide peaks at 2.9–1.5 ppm due to the conversion to the aliphatic ▬CH2 group. The main description of the polymer is exactly the extinction of some characteristic peaks of the double bond in the FT-IR spectrum, and this real is effectively identified herein. Two signals altered in the FT-IR spectrum of the monomer: the stretching vibration band of the vinyl group C〓C at 1630 cm−1 and the absorption signal at 920 cm−1 assigned to the C▬H bending of geminal〓CH2.
7. Functional methacrylate ester monomer and polymer synthesis from photocrosslinkable functional group (pendant chalcone unit) compounds
7.1 Synthesis of hydroxyphenyl-methoxystyryl ketone (hydroxy chalcone)
Substituted benzaldehyde (1 mol) and substituted acetophenone (1 mol) are dissolved in 50 mL of ethyl alcohol and cooled at 18°C. An aqueous NaOH solution (1 mol in 40 mL of distilled water) is then added dropwise with constant mixing and as keeping the temperature constant at 18°C. After stirring the reaction mixture for 12 h at 20°C, it is neutralized with dilute HCl to isolate the compound. The obtained solid matter is filtered through filter paper, washed with ice cold water, dried and recrystallized from ethyl alcohol. Yield: 75%. The synthesis reaction scheme is given in Figure 17.
Figure 17.
Reaction scheme of hydroxyl chalcone.
The structure of hydroxyl chalcone is identified by the FT-IR techniques. FT-IR (cm−1): 3500–3200 (O▬H); 3100–2800 (C▬H); 1690 (>C〓O); 1605 (▬CH〓CH▬); 1570 (aromatic, C〓C).
7.2 Synthesis of methacryloyloxyphenyl-methoxystyryl ketone
In a 250 mL three-necked flask, triethylamine (3 mol) and hydroxyphenyl-methoxystyryl ketone (1 mol) are dissolved in 100 mL of methyl ethyl ketone (MEK) and cooled between 0 and −5°C. Methacryloyl chloride (1.1 mol) in 50 mL of methyl ethyl ketone is then added drop by drop with mixing. After then, the reaction mixture is mixed for 3 h at 20°C and the precipitated quaternary ammonium salt is filtered off. Later, 100 ppm of hydroquinone is added to this solution and the MEK is removed by the vacuum evaporator. The raw product is dissolved in diethyl ether, washed one after another with a 5% aqueous potassium hydroxide solution and distilled water, dried over anhydrous magnesium sulfate (MgSO4) and the diethyl ether is removed by the evaporator. The obtained material is recrystallized from methyl alcohol to get the shining yellow flakes of sübstitue methacryloyloxyphenyl-methoxystyryl ketone. Yield: 80%. The synthesis reaction scheme is given in Figure 18.
Figure 18.
Reaction scheme of methacryloyloxyphenyl-methoxystyryl ketone.
The structure of methacryloyloxyphenyl-methoxystyryl ketone is confirmed by the FT-IR and 1H- and 13C-NMR spectroscopic techniques. FT-IR (cm−1): 3100–2800 (C▬H); 1740 (>C〓O); 1650 (▬C〓O); 1630 (CH2〓C); 1605 (▬CH〓CH▬); 1570 (aromatic, C〓C); 1190 (C▬O▬C). 1H-NMR (CDCl3, TMS): 8.1–6.9 (aromatics ▬H); 6.3–5.78 (CH2〓C, and ▬CH〓CH▬); 3.84 (OCH3); 1.8 (CH3). 13C-NMR (CDCl3, TMS): 178.0 (▬C〓O); 166.8 (>C〓O); 148.1–116.2 (aromatics ▬C); 130.1–122.0 (CH2〓C, and ▬CH〓CH▬); 58.1 (OCH3); 19.1 (CH3).
7.3 Free radical polymerization of substituted methacryloyloxyphenyl-methoxystyryl ketone monomer
Substituted methacryloyloxyphenyl-methoxystyryl ketone is polymerized as a 3 molar solution in MEK using 2,2′-azobisisobutyronitrile (AIBN) as initiator at 70°C. The predetermined quantities of sübstitue methacryloyloxyphenyl-methoxystyryl ketone, the initiator (1 wt.% of monomer) and solvent are placed in a polymerization tube and the mixture is flushed with a slow stream of nitrogen for 20 min. Then, the tube is closed and placed in the thermostated oil bath at 70°C. After the specified time (12 h), the contents are added to excess methyl alcohol to precipitate the polymer. The crude polymer is purified by redissolving in 1,4-dioxane and reprecipitated by methyl alcohol, filtered, washed with methyl alcohol and dried under vacuum at 45°C for constant weight. Yield: 60%. The reaction scheme is shown below (Figure 19).
Figure 19.
Reaction scheme of poly methacryloyloxyphenyl-methoxystyryl ketone.
The structure of poly methacryloyloxyphenyl-methoxystyryl ketone is confirmed by the FT-IR and 1H-NMR spectroscopic techniques. The information is clearly seen in 1H-NMR spectroscopy on polymer formation. The formation of polymer is clearly evident from the disappearing of the two singlets at 6.3 and 5.78 ppm of the vinyl protons and the wide peaks at 2.7–1.3 ppm due to the conversion to the aliphatic ▬CH2 group. The main description of the polymer is exactly the extinction of some characteristic peaks of the double bond in the FT-IR spectrum, and this real is effectively identified herein. Two signals altered in the FT-IR spectrum of the monomer: the stretching vibration band of the vinyl group C〓C at 1630 cm−1 and the absorption signal at 920 cm−1 assigned to the C▬H bending of geminal〓CH2.
8. Conclusion
In this paper, reaction pathway for the synthesis of new methacrylates having pendant amide, dioxolane, benzofuran and chalcone groups are described. Molecular structure information such as reaction scheme, Fourier transform infrared (FT-IR) and nuclear magnetic resonance spectroscopy of all the compounds is given. All of the methacrylates are used as photodegradable packaging materials and photoresists for microlithography. The increasing utility of photosensitive polymers in many applications such as microelectronics, printing and UV-curable lacquers, and inks is provided us with an incentive to obtain novel polymers.
Conflict of interest
The authors declare no conflict of interest.
\n',keywords:"activated (meth)acrylates, α-chloro-N-aryl acetamides, dioxolane, benzofuran, chalcone, functional polymers",chapterPDFUrl:"https://cdn.intechopen.com/pdfs/69528.pdf",chapterXML:"https://mts.intechopen.com/source/xml/69528.xml",downloadPdfUrl:"/chapter/pdf-download/69528",previewPdfUrl:"/chapter/pdf-preview/69528",totalDownloads:222,totalViews:0,totalCrossrefCites:0,totalDimensionsCites:0,hasAltmetrics:0,dateSubmitted:"February 14th 2019",dateReviewed:"September 17th 2019",datePrePublished:"January 22nd 2020",datePublished:"March 11th 2020",dateFinished:null,readingETA:"0",abstract:"Generally, the words “reactive polymers” and “functional polymers” mean the same thing and are used interchangeably in most studies and describe cross-linked (insoluble) bead-structured resins containing chemically reactive functional groups. In this way, reactive polymers are widely used as polymeric reagents or polymer supports in biochemical and chemical applications. Functional (meth)acrylates referred here to supply “functional esters” ruins as a general reactive group precursor. In other sense, the leaving (activating) groups of these monomers may easily react with the alcohols and amines carrying the desired reactive groups and therefore, in general, provide a single reaction step for the synthesis of reactive polymers. In this paper, we suggest new routes for a new (meth)acrylate-based monomers and polymers. Also, the synthesis of a serial new (meth)acrylate esters including amide, dioxolane, benzofuran, and chalcone groups is described.",reviewType:"peer-reviewed",bibtexUrl:"/chapter/bibtex/69528",risUrl:"/chapter/ris/69528",book:{slug:"organic-polymers"},signatures:"Cengiz Soykan",authors:[{id:"295591",title:"Prof.",name:"Cengiz",middleName:null,surname:"Soykan",fullName:"Cengiz Soykan",slug:"cengiz-soykan",email:"cengizsoykan@usak.edu.tr",position:null,institution:{name:"Usak University",institutionURL:null,country:{name:"Turkey"}}}],sections:[{id:"sec_1",title:"1. Introduction",level:"1"},{id:"sec_2",title:"2. Functional methacrylate ester monomer and polymer synthesis from oxirane compounds",level:"1"},{id:"sec_2_2",title:"2.1 Synthesis of aryloxy-2,3-epoxy propane (oxirane)",level:"2"},{id:"sec_3_2",title:"2.2 Synthesis of aryloxy-2-hydroxypropyl methacrylate monomer",level:"2"},{id:"sec_4_2",title:"2.3 Free radical polymerization of aryloxy-2-hydroxypropyl methacrylate monomer",level:"2"},{id:"sec_6",title:"3. Functional methacrylate ester monomer and polymer synthesis from arylacetylhalide compounds",level:"1"},{id:"sec_6_2",title:"3.1 Synthesis of arylacetylhalide",level:"2"},{id:"sec_7_2",title:"3.2 Synthesis of aryloxycarbonyl methyl methacrylate monomer",level:"2"},{id:"sec_8_2",title:"3.3 Free radical polymerization of aryloxycarbonyl methyl methacrylate monomer",level:"2"},{id:"sec_10",title:"4. Functional methacrylate ester monomer and polymer synthesis from α-chloro-N-arylacetamide compounds",level:"1"},{id:"sec_10_2",title:"4.1 Synthesis of α-chloro-N-arylacetamide",level:"2"},{id:"sec_11_2",title:"4.2 Synthesis of arylamido methyl methacrylate monomer",level:"2"},{id:"sec_12_2",title:"4.3 Free radical polymerization of arylamido methyl methacrylate monomer",level:"2"},{id:"sec_14",title:"5. Functional methacrylate ester monomer and polymer synthesis from aryl-1,3-dioxolane compounds",level:"1"},{id:"sec_14_2",title:"5.1 Synthesis of (aryl-1,3-dioxolane-4-yl) methanol",level:"2"},{id:"sec_15_2",title:"5.2 Synthesis of (aryl-1,3-dioxolane-4-yl) methyl acrylate monomer",level:"2"},{id:"sec_16_2",title:"5.3 Free radical polymerization of arylamido methyl methacrylate monomer",level:"2"},{id:"sec_18",title:"6. Functional methacrylate ester monomer and polymer synthesis from benzofuran compounds",level:"1"},{id:"sec_18_2",title:"6.1 Synthesis of acetyl benzofuran",level:"2"},{id:"sec_19_2",title:"6.2 Synthesis of bromo-acetyl benzofuran",level:"2"},{id:"sec_20_2",title:"6.3 Synthesis of acetyl benzofuryl methyl methacrylate monomer",level:"2"},{id:"sec_21_2",title:"6.4 Free radical polymerization of acetyl benzofuryl methyl methacrylate monomer",level:"2"},{id:"sec_23",title:"7. Functional methacrylate ester monomer and polymer synthesis from photocrosslinkable functional group (pendant chalcone unit) compounds",level:"1"},{id:"sec_23_2",title:"7.1 Synthesis of hydroxyphenyl-methoxystyryl ketone (hydroxy chalcone)",level:"2"},{id:"sec_24_2",title:"7.2 Synthesis of methacryloyloxyphenyl-methoxystyryl ketone",level:"2"},{id:"sec_25_2",title:"7.3 Free radical polymerization of substituted methacryloyloxyphenyl-methoxystyryl ketone monomer",level:"2"},{id:"sec_27",title:"8. 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Journal of Hazardous Materials. 2009;169:593-598. DOI: 10.1016/j.jhazmat.2009.03.146'},{id:"B18",body:'Soykan C, Şahan A, Yakuphanoğlu F. Synthesis and semi-conducting properties of novel 2-(4-chloro-1-naphtyloxy)-2-oxoethyl methacrylate with 2-(dimethylamino)ethyl methacrylate copolymers, quaternized amino groups. Journal of Macromolecular Science, Part A: Pure and Applied Chemistry. 2011;48(2):169-176. DOI: 10.1080/10601325.2011.537537'},{id:"B19",body:'Ari H, Soykan C, Özpozan T. Preparation of organic/inorganic hybrid materials using aggregates of poly{2-methyl-N-[2-(phenylthio)phenyl]acrylamide-co-2-(trimethylsyloxy)ethyl methacrylate} as precursor and vibrational investigation of the polymerization. Journal of Macromolecular Science, Part A: Pure and Applied Chemistry. 2013;50(10):1022-1041. DOI: 10.1080/10601325.2013.821847'},{id:"B20",body:'Açıkbaş Y, Erdoğan M, Çapan R, Soykan C. Characterization and gas sensing properties of Langmuir-Blodgett thin films of poly(ClNOEMA-co-DEAEMA). Sensor Letters. 2016;14:474-483. DOI: 10.1166/sl.2016.3636'},{id:"B21",body:'Açıkbaş Y, Çapan R, Erdoğan M, Bulut L, Soykan C. Optical characterization and swelling behaviour of Langmuir-Blodgett thin films of a novel poly[styrene(ST)-co-glycidyl methacrylate (GMA)]. Sensors and Actuators B: Chemical. 2017;241:1111-1120. DOI: 10.1016/j.snb.2016.10.025'},{id:"B22",body:'Patel MB, Patel SA, Ray A, Patel KH. Synthesis, characterization, and antimicrobial activity of acrylic copolymers. Journal of Applied Polymer Science. 2003;89(4):895-900. DOI: 10.1002/app.11970'},{id:"B23",body:'Patel MP, Shah B, Ray A, Patel KH. Acrylic homo- and co-polymers based on 2,4-dichlorophenyl methacrylate and 8-quinolinyl methacrylate. Journal of Polymer Science-Taiwan. 2004;11(1):65-73. DOI: 10.1023/B:JPOL.0000021779.30811.48'},{id:"B24",body:'Patel MV, Dolia MB, Patel JN, Patel RM. Synthesis and characterization of novel acrylic copolymers: Determination of monomer reactivity ratios and biological activity. Reactive and Functional Polymers. 2005;65(3):195-204. DOI: 10.1016/j.reactfunctpolym.2005.08.002'},{id:"B25",body:'Patel JN, Patel JR, Patel KH, Patel MP, Patel MR. Acrylic copolymers basedo phenol: Synthesis, characterization, and antimicrobial activity. Journal of Macromolecular Science, Part A Pure and Applied Chemistry. 2007;44(4-6):395-402. DOI: 10.1080/10601320601188109'},{id:"B26",body:'Patel MG, Patel HJ, Patel JR, Patel KH. Development and applications of novel acrylic copolymers. International Journal of Polymeric Materials. 2008;57(2):165-176. DOI: 10.1080/00914030701486179'},{id:"B27",body:'Patel JR, Patel KH, Patel RM. Reactivity ratio of novel acrylic copolymer by NMR spectroscopy. Colloid & Polymer Science. 2009;287(1):85-90. DOI: 10.1007/s00396-008-1943-6'},{id:"B28",body:'Patel HJ, Patel MG, Patel AK, Patel KH. Synthesis, characterization and antimicrobial activity of important heterocyclic acrylic copolymers. Express Polymer Letters. 2008;2(10):727-734. DOI: 10.3144/expresspolymlett.2008.86'},{id:"B29",body:'Patel RT, Patel KH, Patel AR, Patel RM. Kinetic of 8-quinolinyl methacrylate polymerization by differential scanning calorimetry. International Journal of Polymeric Materials and Polymeric Biomaterials. 2000;46:71-79. DOI: 10.1080/00914030008054842'},{id:"B30",body:'Vijayanand PS, Kato S, Kojima T. Synthesis and characterization of 3,5-dimethoxyphenyl methacrylate and methyl methyacrylate copolymers: Determination of monomer reactivity ratios. Journal of Macromolecular Science, Part A: Pure and Applied Chemistry. 2007;44(3):277-283. DOI: 10.1080/10601320601077302'},{id:"B31",body:'Zhang R, Yang J, Sun W, Shen Z. Synthesis and characterization of poly [4-(2-thiazolylazo) phenyl methacrylate]-co-poly(methyl methacrylate). Journal of Applied Polymer Science. 2007;103(4):2152-2157. DOI: 10.1002/app.25041'},{id:"B32",body:'Thamizharasi S, Gnanasundaram P, Reddy BSR. Copolymerization of 4-acetyl phenylacrylate with methacrylate and butyl methacrylate: Synthesis, characterization and reactivity ratios. European Polymer Journal. 1997;33(9):1487-1494. DOI: 10.1016/S0014-3057(96)00270-4'},{id:"B33",body:'Stanek LG, Heilmann SM, Gleason WB. Synthesis and monomer reactivity ratios of methyl methacrylate and 2-vinyl-4,4′-dimethylazlactone copolymers. Journal of Polymer Science, Part A: Polymer Chemistry. 2003;41:3027-3037. DOI: 10.1002/pola.10897'},{id:"B34",body:'Loubat C, Batt-Coutrot D, Guyot B, Robin JJ, Boutevin B. Synthesis and monomer reactivity ratios of ethyl α-acetoxyacrylate and acrylic acid copolymers. Polymer International. 2005;54(11):1557-1563. DOI: 10.1002/pi.1884'}],footnotes:[],contributors:[{corresp:"yes",contributorFullName:"Cengiz Soykan",address:"cengizsoykan@usak.edu.tr",affiliation:'
Department of Materials Science and Nanotechnology, Faculty of Engineering, University of Uşak, Uşak, Turkey
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Massuda",slug:"lillian-a.-massuda"}]},{id:"67521",title:"Lignin as Sustainable Antimicrobial Fillers to Develop PET Multifilaments by Melting Process",slug:"lignin-as-sustainable-antimicrobial-fillers-to-develop-pet-multifilaments-by-melting-process",totalDownloads:440,totalCrossrefCites:1,signatures:"Juliette Minet, Aurélie Cayla and Christine Campagne",authors:[{id:"229606",title:"Dr.",name:"Aurélie",middleName:null,surname:"Cayla",fullName:"Aurélie Cayla",slug:"aurelie-cayla"},{id:"303114",title:"Prof.",name:"Christine",middleName:null,surname:"Campagne",fullName:"Christine Campagne",slug:"christine-campagne"},{id:"303115",title:"Mrs.",name:"Juliette",middleName:null,surname:"Minet",fullName:"Juliette Minet",slug:"juliette-minet"}]}]},relatedBooks:[{type:"book",id:"6387",title:"Polyester",subtitle:"Production, Characterization and Innovative Applications",isOpenForSubmission:!1,hash:"3a1fd3a0981aecc295467e1d7650c1af",slug:"polyester-production-characterization-and-innovative-applications",bookSignature:"Nurhan Onar Camlibel",coverURL:"https://cdn.intechopen.com/books/images_new/6387.jpg",editedByType:"Edited by",editors:[{id:"198613",title:"Dr.",name:"Nurhan",surname:"Onar Camlibel",slug:"nurhan-onar-camlibel",fullName:"Nurhan Onar Camlibel"}],equalEditorOne:null,equalEditorTwo:null,equalEditorThree:null,productType:{id:"1",chapterContentType:"chapter",authoredCaption:"Edited by"},chapters:[{id:"59228",title:"Introductory Chapter: Introduction to “Polyester – Production, Characterization and Innovative Applications”",slug:"introductory-chapter-introduction-to-polyester-production-characterization-and-innovative-applicatio",signatures:"Nurhan Onar Camlibel",authors:[{id:"198613",title:"Dr.",name:"Nurhan",middleName:null,surname:"Onar Camlibel",fullName:"Nurhan Onar Camlibel",slug:"nurhan-onar-camlibel"}]},{id:"58300",title:"PET Bottle Recycling for Sustainable Textiles",slug:"pet-bottle-recycling-for-sustainable-textiles",signatures:"Esin Sarioğlu and Hatice Kübra Kaynak",authors:[{id:"117486",title:"Dr.",name:"Hatice Kubra",middleName:null,surname:"Kaynak",fullName:"Hatice Kubra Kaynak",slug:"hatice-kubra-kaynak"},{id:"216179",title:"Dr.",name:"Esin",middleName:null,surname:"Sarıoğlu",fullName:"Esin Sarıoğlu",slug:"esin-sarioglu"}]},{id:"58335",title:"Flame-Retardant Unsaturated Polyester Resins: An Overview of Past and Recent Developments",slug:"flame-retardant-unsaturated-polyester-resins-an-overview-of-past-and-recent-developments",signatures:"Ewa Kicko-Walczak and Grażyna Rymarz",authors:[{id:"221591",title:"Associate Prof.",name:"Ewa",middleName:"Janina",surname:"Kicko-Walczak",fullName:"Ewa Kicko-Walczak",slug:"ewa-kicko-walczak"},{id:"231231",title:"Mr.",name:"Grazyna",middleName:null,surname:"Rymarz",fullName:"Grazyna Rymarz",slug:"grazyna-rymarz"}]},{id:"59499",title:"Polyester Usage in Manufacturing of Electrical and Mechanical Products and Assemblies",slug:"polyester-usage-in-manufacturing-of-electrical-and-mechanical-products-and-assemblies",signatures:"Ahmad Nawaz, Bilal Islam, M. Sadiq Khattak, Liaquat Ali, Umar\nSaleem, Azmat Ullah, M. Zafar Ijaz and Weiguo Mao",authors:[{id:"222043",title:"Associate Prof.",name:"Ahmad",middleName:null,surname:"Nawaz",fullName:"Ahmad Nawaz",slug:"ahmad-nawaz"},{id:"238325",title:"Mr.",name:"Bilal",middleName:null,surname:"Islam",fullName:"Bilal Islam",slug:"bilal-islam"},{id:"238326",title:"Dr.",name:"Muhammad",middleName:null,surname:"Sadiq Khattak",fullName:"Muhammad Sadiq Khattak",slug:"muhammad-sadiq-khattak"},{id:"238458",title:"Prof.",name:"Weiguo",middleName:null,surname:"Mao",fullName:"Weiguo Mao",slug:"weiguo-mao"}]},{id:"59092",title:"A Case Study: Particulate-Filled Polyester Hybrid Laminated Composites",slug:"a-case-study-particulate-filled-polyester-hybrid-laminated-composites",signatures:"Muhammad Azeem Munawar, Dirk Wolfram Schubert, Shahzad\nMaqsood Khan, Nafisa Gull, Atif Islam, Muhammad Atiq Ur Rehman\nand Monika M. 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\n
1. Introduction
\n
Voltammetry is an electrochemical technique for current-voltage curves, from which electrode reactions at electrode-solution interfaces can be interpreted. Since current-voltage curves, called voltammograms, include sensitive properties of solution compositions and electrode materials, their analysis provides not only chemical structures and reaction mechanisms on a scientific basis but also electrochemical manufacture on an industrial basis. The voltammograms vary largely with measurement time except for steady-state measurements, and so it is important to pay attention to time variables. Voltage is a controlling variable in conventional voltammetry, and the current is a measured one detected as a function of applied voltage at a given time.
\n
The equipment for voltammetry is composed of electrodes, solution, and electric instruments for voltage control. Electrodes and electric instruments are keys of voltammetry. Three kinds of electrodes are desired to be prepared: a working electrode, a counter one, and a reference one. The three will be addressed below.
\n
Let us consider a simple experiment in which two electrodes are inserted into a salt-included aqueous solution. When a constant current is applied to the two electrodes, reaction 2H+ + 2e− → H2 may occur at one electrode, and reaction 2OH− → H2O2 + 2e− occurs at the other. The current is the time variation of the electric charge, and hence it is a kind of reaction rate at the electrode. Since the applied current is a sum of the two reaction rates, one being in the positive direction and the other being in the negative, it cannot be attributed to either reaction rate. A technique of attributing the reactions is to use an electrode with such large area that an uninteresting reaction rate may not become a rate-determining step. This electrode is called a counter electrode. The current density at the counter electrode does not specifically represent any reaction rate. In contrast, the current density at the electrode with a small area stands for the interesting reaction rate. This electrode is called a working electrode. It is the potential difference, i.e., voltage, at the working electrode and in the solution that brings about the electrode reaction. However, the potential in the solution cannot be controlled with the working electrode or the counter one. The control can be made by mounting another electrode, called a reference electrode, which keeps the voltage between an electrode and a solution to be constant. However, the constant value cannot be measured because of the difference in phases. A conventionally employed reference electrode is silver-silver chloride (Ag-AgCl) in high concentrated KCl aqueous solution.
\n
An electric instrument of operating the three electrodes is a potentiostat. It has three electric terminals: one being a voltage follower for the reference electrode without current, the second being a current feeder at the counter electrode, and the third being at the working electrode through which the current is converted to a voltage for monitoring. A controlled voltage is applied between the working electrode and the reference one. These functionalities can readily be attained with combinations of operational amplifiers. A drawback of usage of operational amplifiers is a delay of responses, which restricts current responses to the order of milliseconds or 10 kHz frequency.
\n
Voltammetry includes various types—linear sweep, cyclic, square wave, stripping, alternating current (AC), pulse, steady-state microelectrode, and hydrodynamic voltammetry—depending on a mode of the potential control. The most frequently used technique is cyclic voltammetry (CV) on a time scale of seconds. In contrast, currently used voltammetry at time as short as milliseconds is AC voltammetry. We describe here the theory and tips for practical use of mainly the two types of voltammetry.
\n
\n
\n
2. Theory
\n
The theory of voltammetry is to obtain expressions for voltammograms on a given time scale or for those at a given voltage. First of all, it is necessary to specify rate-determining steps of voltammograms. There are three types of rate-determining steps under the conventional conditions: diffusion of redox species in solution near an electrode, adsorption on an electrode, and charging processes at the double layer (DL). Electric field-driven mass transport, called electric migration, belongs to rare experimental conditions, and hence it is excluded in this review. When a redox species in solution is consumed or generated at an electrode, it is supplied to or departed from the electrode by diffusion unless solution is stirred. When it is accumulated on the electrode, the change in the accumulated charge by the redox reaction provides the current. Whenever electrode voltage is varied with the time, the charging or discharging of the DL capacitor causes current. Therefore, the three steps are frequently involved in electrochemical measurements.
\n
A mass transport problem on voltammetry is briefly described here. The redox species is assumed to be transported by one-directional (x) diffusion owing to heterogeneous electrode reactions. Then, the flux is given by f = −D(∂c/∂x), where c and D are the concentration and the diffusion coefficient of the redox species, respectively. Redox species in solution causes some kinds of chemical reaction through chemical reaction rates, h(c, t). Then the reaction rate is the sum of the diffusional flux and the chemical reaction rate, ∂c/∂t = −∂f/∂x − h(c, t). Here the equation for h = 0 is called an equation of continuum. Eliminating f with the above equation on the assumption of a constant value of D yields ∂c/∂t = D(∂2c/∂x2) − h(c, t). This is an equation for diffusion-chemical kinetics. The expression at h = 0 is the diffusion equation. A boundary condition with electrochemical significance is the control of c at the electrode surface with a given electrode potential. If the redox reaction occurs in equilibrium with the one-electron transfer at the electrode, the Nernst equation for the concentrations of the oxidized species, co, and the reduced one, cr, holds.
The other conditions are concentrations in the bulk (x → ∝) and the initial conditions.
\n
\n
2.1. Diffusion-controlled current
\n
If the mass transport is controlled only by x-directional diffusion, cr and co are given by the diffusion equations, ∂c/∂t = D(∂2c/∂t2) for c = cr or co. An electrochemically significant quantity is not concentration in any x and t, but a relation between the surface concentrations and the current (the flux at x = 0). On the assumption of Do = Dr = D, of the initial and boundary conditions, (cr)t = 0 = c*, (co)t = 0 = 0, and (cr)x = ∞ = c*, (co)x = ∞ = 0, a solution of the initial-boundary problem is given by [1].
where j is the current density. The common value of the diffusion coefficients yields co + cr = c* for any x and t. Inserting this relation and Eq. (3) into the Nernst equation, (co)x = 0 = c*/[1 + exp[−F(E − Eo)/RT]], we obtain the integral equation for j as a function of t or E.
\n
\n
2.1.1. Linear sweep voltammetry by diffusion
\n
When the voltage is linearly swept with the time at a given voltage scan rate, v, from the initial potential Ein, Eq. (3) through the combination with the Nernst equation becomes
The above Abel’s integral equation can be solved by Laplace transformation. When the time variation is altered to the voltage variation through E = Ein + vt, the current density is expressed as
where ζ = (E − Eo)F/RT and ζi = (Ein − Eo)F/RT. Evaluation of the integral has to resort to numerical computation. Current at any voltage should be proportional to v1/2, as can be seen in Eq. (5). The voltammogram for v > 0 rises up from Eo, takes a peak, and then deceases gradually with the voltage. The decrease in the current is obviously ascribed to relaxation by diffusion. The peak current density is expressed by
at Ep = Eo + 0.029 V at 25°C, where 0.446 comes from the numerical calculation of the integral of Eq. (5).
\n
Practical voltage-scan voltammetry is not simply linear sweep but cyclic voltammetry (CV), at which applied voltage is reversed at a given voltage in the opposite direction. The theoretical evaluation of the voltammogram should be at first represented in the integral form with the time variation and then express the time as the voltage. One of the features of the diffusion-controlled cyclic voltammograms is the difference between the anodic peak potential and the cathodic one, ΔEp (in Figure 1), of which value is 59 mV at 25°C.
\n
Figure 1.
Voltammograms calculated from Eq. (5) for v = (a) 180, (b) 80 and (c) 20 mV s−1.
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\n
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2.1.2. AC voltammetry by diffusion
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AC voltammetry can be performed when the time variation of voltage is given by E = Edc + V0eiωt, where ω is the frequency of applied AC voltage, i is the imaginary unit, V0 is its voltage amplitude, and Edc is the DC voltage. A conventional value of V0 is 10 mV. When this voltage form is inserted into Eq. (3) together with the Nernst equation, the AC component of the current density is represented by [2].
A voltammogram (j vs. Edc) at a given frequency takes a bell shape, which is expressed by sech2{(Edc − Eo)/RT}. The functional form of sech2 is shown in Figure 2. The peak current appears at Edc = Eo.
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Figure 2.
Voltammogram calculated from Eq. (10).
\n
The AC-impedance technique often deals with the real impedance, Z1, = 1/2Y1 and the imaginary one, Z2 = −1/2Y1, where Y1 is the real admittance given by
Here Y2 is the imaginary admittance, equal to Y1. Since Z1 = −Z2, the Nyquist plot, i.e., −Z2 vs. Z1, is a line with the slope of unity. The term 1 + i in Eq. (7) has come from (Dω)1/2, originating from (Diω)1/2. Therefore, it can be attributed to diffusion. In other words, diffusion produces the capacitive component as a delay.
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\n
\n
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2.2. Adsorption-controlled current
\n
When the redox species with reaction R = O + e− is adsorbed on the electrode and has no influence from the redox species in the solution, the sum of the surface concentrations of R and O is a constant, Γ*. Then the surface concentration of the oxidized species, Γo, is given by the Nernst equation:
The time derivative of the redox charge corresponds to the current density, j = d(FΓo)/dt. Application of the condition of voltage sweep, E = Ein + vt, to Eq. (9) yields.
The voltammogram takes a bell shape (Figure 2), of which peak is at E = Eo, similar to the AC voltammogram. The current at any voltage is proportional to v. Since the negative-going scan of the voltage provides negative current values, the cyclic voltammogram should be symmetric with respect to the I = 0 axis. The peak current is expressed as jp = F2Γ*v/4RT. The width of the wave at jp/2 is 90 mV at 25°C.
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\n
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\n
2.3. Capacitive current
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Since a phase has its own free energy, contact of two phases provides a step-like gap of the free energy, of which gradient brings about infinite magnitude of force. In order to relax the infinity, local free energy varies from one phase to the other as smoothly as possible at the interface. The large variation of the energy is compensated with spontaneously generated space variations of voltage, i.e., the electric field, which works as an electric capacitor. The capacitance at solution-electrode interface causes orientation of dipoles and nonuniform distribution of ionic concentration, of which layer is called an electric double layer (DL).
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When the time variation of the voltage is applied to the DL capacitance, Cd, the definitions of the capacitance (q = CdV) and the current lead
where Cd generally depends on the time. This dependence is significant for understanding experimentally observed capacitive currents.
\n
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2.3.1. Capacitance by AC impedance
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The DL capacitance has exhibited the frequency dispersion expressed by Cd = (Cd) 1Hzf −λ, called the constant phase element [3, 4, 5] or power law [6, 7], where λ is close to 0.1. Inserting this expression and V = V0eiωt into Eq. (11) yields
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\n\nI\n=\n\n\ni\n+\nλ\n\n\n\nωC\nd\n\nV\n\nE12
\n
This is a simple sum of the real part of the current and the imaginary one, indicating that the equivalent circuit should be a parallel combination of a capacitive component and a resistive one, both depending on frequency. Since the ratio, −Z2/Z1, for Eq. (12) is 1/λ, the Nyquist plots have slopes less than 10 rather than infinity.
\n
\n
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2.3.2. Capacitive current by CV
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If the capacitive charge is independent of the time, the capacitive current should be I = d(CV)/dt = C(E − Eo)/v. Therefore, it takes a horizontal positive (v > 0) and a negative line (v < 0), as shown in Figure 3 (dashed lines). When the time dependence of C, i.e., Cd = (Cd)0t−λ, is applied to Eq. (11), for the forward and the backward scans, respectively, we have
Capacitive voltammograms by CV at v= 0.5 V s−1 for (dashed lines) the ideal capacitance and for Eq. (13) (solid curves) at λ = 0.2.
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The variation of CV computed from Eq. (13) (Figure 3, solid curves) is similar to our conventionally observed capacitive waves.
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3. Tips of voltammetric analysis
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Voltammograms can identify an objective species by comparing a peak potential with a table of redox potentials and furthermore determine its concentration from the peak current. Their results are, however, sometimes inconsistent with data by methods other than electrochemical techniques if one falls in some pitfalls of analytical methods of electrochemistry. For example, a peak potential is influenced by a reference electrode and solution resistance relevant to methods. Peak currents are varied complicatedly with mass transport modes as well as associated chemical reactions. Since the theory on voltammetry covers only some restricted experimental conditions, it can rarely interpret the experimental data successfully. This review is devoted to some voltammetric tips which can lead experimenters to reasonable interpretation.
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3.1. Understanding outline of voltammograms
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It is rare to observe a reversible voltammogram in which both oxidation and reduction waves appear in a symmetric form with respect to the potential axis at a similar peak potential, as in Figure 1. Frequently observed voltammograms are irreversible, i.e., either a cathodic or an anodic wave appears; a value of a cathodic peak current is quite different from the anodic one in magnitude; a cathodic peak potential is far from the anodic one. These complications are ascribed to chemical reactions and/or phase transformation after the charge-transfer reaction. A typical example is deposition of metal ions on an electrode. The complications can be interpreted by altering scan rates and reverse potentials.
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A wave at a backward scan is mostly attributed to electrode reactions generated by experimenters rather than to species latently present in the solution. That is, it is artificial. It is caused either by the reaction of the wave at the forward scan or the reaction of the rising-up current just before the reverse potential. A source of the backward wave can be found by changing the reverse potentials.
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Some voltammograms have more than two peaks at one-directional scan. The appearance of the two can be interpreted as a two-step sequential charge-transfer reaction. However, multiple waves appear also by combinations of chemical reactions and adsorption. The peak current and the charge for this case are quite different from the predicted ones, as will be described in Section 3.2. Change in scan rates may be helpful for interpreting the multiple waves.
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3.2. Shape and values of peaks
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It is possible to predict theoretically a controlling step of voltammograms from their shape (a bell type corresponding to an adsorption wave or a draw-out type corresponding to a diffusion wave). However, the shape strongly depends on chemical complications, adsorption, and surface treatment of the electrodes. When redox species in solution is partially adsorbed on an electrode, the electrode process is far from a prediction because of very high concentration in the adsorbed state. A draw-out-shaped wave can be observed even for the adsorbed control. It is important to estimate which state the reacting species takes on the electrode. Potentials representing of voltammetric features do not express a controlling step in reality although the theory does. One should pay attention to the current. The peak current controlled by diffusion with one-electron transfer is given by Ip = 0.27 cAv1/2 μA (c, bulk concentration mM; A, electrode area mm2; v, potential sweep rate mV s−1). The microelectrode behavior sometimes comes in view at v < 10 mV s−1, A < 0.1 mm2, so the measured current is larger than the estimated value. On the other hand, the peak current controlled by adsorption is given by Ip = 1.6 Av nA when one redox molecule is adsorbed at 1 nm2 on the electrode. The voltammogram by adsorption often differs from the ideal bell shape due to adsorbed molecular interaction and DL capacity. Division of the area of the peak by the scan rate yields the amount of adsorbed electricity. Comparison of this with the anticipated amount of adsorption may be helpful for understanding the electrode process.
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3.3. Deviation of ΔEp from theoretical values
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The peak potential difference ΔEp between the oxidation wave and the reduction wave (Figure 1) has been used for a prediction of the reaction mechanism. For example, ΔEp = 60 mM suggests the diffusion-controlled current accompanied by one-electron exchange, whereas ΔEp = 30 mM infers a simultaneous reaction with two electrons. Then what would happen for 120 mV which is sometimes found? A half-electron reaction might not be accepted. Potential shift over 60 mV occurs by chemical complications. In contrast, the voltammogram by adsorbed species shows theoretically a bell shape with the width, E1/2 = 90 mV, at the half height of the peak (Figure 2). This value is based on the assumption of the absence of interaction among adsorbed species. However, adsorption necessarily yields such high concentrations as strong interaction.
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It is necessary to pay attention to the validity of analyzing ΔEp and E1/2. The peak potential is the first derivative of a voltammogram. Since ΔEp is a difference between the two peaks, it is actually the second-order derivative of the curves in the view of accuracy. In other words, the accuracy of ΔEp is lower than that of peak current. Furthermore, peak potentials as well as E1/2 readily vary with scan rates owing to chemical reactions and solution resistance. One should use the peak current for data analysis instead of the potentials.
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3.4. Criteria of diffusion-controlled currents
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Voltammograms of a number of redox species have been reported to be diffusion controlled from a relationship between Ip and v1/2. The redox species exhibiting diffusion-controlled current is, however, limited to ferrocenyl derivatives under conventional conditions. Voltammograms even for [Fe(CN)6]3−/4− and [Ru(NH3)6]3+ are deviated from the diffusion control for a long-time measurement. Why have many researchers assigned voltammograms to be the diffusion-controlled step? The proportionality of Ip to v1/2 in Eq. (6) has been confused with the linearity, Ip = av1/2 + b (b ≠ 0). The plot for the adsorption control (Ip = kv) also shows approximately a linear relation for Ip vs. v1/2 plot in a narrow domain of v, as shown in Figure 4B. The opposite is true (Figure 4A). Therefore, it is the intercept that determines a controlling step of either the diffusion or adsorption. Some may say that the intercept can be ascribed to a capacitive current. If so, the peak current should be represented by Ip = av1/2 + bv, which exhibits neither linear relation with v1/2 nor v.
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Figure 4.
Plots of Ip of (A) K3Fe(CN)6 and (B) polyaniline-coated electrode against v1/2 and v. Both plots show approximately linear relations.
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There is a simple method of determining a controlling step either by diffusion or adsorption. Current responding to diffusion-controlled potential at a disk electrode in diameter less than 0.1 mm would become under the steady state after a few seconds [8]. Adsorption-limited current should become zero soon after the potential application. Many redox species, however, show gradual decrease in the current because reaction products generate an adsorbed layer which blocks further electrode reactions.
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3.5. Plots of Ip against Ep
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It is well known that currents vary not only with applied voltage but also with the time. It is not popular, however, to discuss quantitatively time dependence of CV voltammograms. Enhancing v generally increases the current and causes the peak potential to shift in the direction of the scan. A reason for the former can be interpreted as generation of large current at a shorter time (see Eqs. (6) and (10)), whereas the latter is ascribed to a delay of reaction responses as well as a voltage loss of the reaction by solution resistance. Then the voltage effective to the reaction is lower than the intended voltage, and so the observed current may be smaller than the predicted one. Although Ip is related strongly with Ep, the relationship has rarely been examined quantitatively.
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A technique of analyzing the potential shift is to plot Ip against Ep, [9] as shown in Figure 5. If the plots on the oxidation side (Ip > 0) and the reduction side (Ip < 0) fall each on a straight line, the slope may represent conductivity. If values of both slopes are equal, the slope possibly stands for the conductivity of the solution or membrane regardless of the electrode reaction. The potential extrapolated to the zero current on each straight line should be close to the formal potential. Since this plot is simple technically, the analytical result is more reliable than at least discussion of time dependence of Ep.
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Figure 5.
Plots of Ip vs. Ep by CV of the first (circles) and the second (triangles) peak of tetracyanoquinodimethane (TCNQ), and ferrocene (squares) in 0.2 M (CH3)4NPF6 included acetonitrile solution when scan rates were varied, where triangles were displayed by 0.4 V shift.
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3.6. Meaning of n3/2 in the equation for peak current
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Most researchers have quoted the Randles-Sevcik equation, jp = 0.446 (nF)3/2c*(Dv/RT)1/2, for the diffusion-controlled peak current without hesitation, where n is the electron transfer number of the reaction. According to Faraday’s law, the electrolytic quantity is proportional to nc*. Why is the peak current proportional to n3/2 instead of n? Let us consider voltammetry of metal nanoparticles (about 25 nm in diameter) composed of 106 metal atoms dispersed in solution. Faraday’s law predicts that the current is 106 times as high as the current by the one metal atom. However, Randles-Sevcik equation predicts the current further (106)1/2 = 1000 times as large, just by the effect of the potential scan. The order 3/2 is specific to CV. The order of n for AC current and pulse voltammetry is 2 [10]. On the other hand, the diffusion-controlled steady-state currents at a microelectrode and a rotating disk electrode are proportional to n. Comparing the differences in the order by methods, we can predict that the time variation of the voltage increases the power of n.
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Let a potential width from a current-rising potential to Ep be denoted by ΔE. When an n-electron transfer reaction occurs through the Nernst equation at which F in Eq. (1) is replaced by nF, the concentration-potential curve takes the slope n times larger than that at n = 1 (see co/cr ≅ nF(E − Eo)/RT near E = Eo in Eq. (1)). Then we have (ΔE)n = (ΔE)n = 1/n. The period of elapsing for (ΔE)n becomes shorter by 1/n, as if v might be larger by n times. Then v in Eq. (6) should be replaced by (nv)1/2. Combining this result with the flux j/nF, the current becomes n3/2 times larger than that at n = 1. Therefore, the factor n3/2 results from the Nernst equation. This can be understood quantitatively by replacing F in Eq. (3) by nF. There are quite a few reactions for n ≥ 2 both for Nernst equation and in the bulk as stable species. The term n3/2 is valid only for a concomitant charge-transfer reaction, i.e., simultaneous occurrence n-electron transfer rather than a step-by-step transfer. Apparent two-electron transfer reactions in the bulk, for example, Cu, Fe, Zn, and Pb, cause other reactions immediately after the one-electron transfer.
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3.7. Area of counter electrode
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An electrochemical response is observed as a sum of the half reactions at the two electrodes. In order to extract the reaction at the working electrode, a conventional technique is to increase the area of the counter electrode so that the reaction at the counter electrode can be ignored. If the counter electrode area is increased by 20 times the area of the working electrode, the observed current represents the reaction of the working electrode with an error of 5%. Let us consider the experiment in which nanoparticles of metal are coated on a working electrode for obtaining capacitive currents or catalyst currents. Then, the actual area of the working electrode can be regarded as the area of the metal particles measured by the molecular level. Then, the area will be several thousand times the geometric area so that the observed current may represent the reaction at the counter electrode. This kind of research has frequently been found in work on supercapacitors. On the other hand, if the electrode reaction is diffusion controlled, the current is determined by the projected area of the diffusion layer. Then the current is not affected by the huge surface area of nanoparticles.
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It is important to examine whether or not a reaction is controlled by at a counter electrode. A simple method is to coat nanoparticles also on the counter electrode. Then the current in the solution may become so high that the potential of the working electrode cannot be controlled. It is better to use a two-electrode system. Products at the counter electrode are possible sources of contaminants through redox cycling.
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3.8. Functionality of reference electrode
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The Ag-AgCl electrode is most frequently used as a reference electrode in aqueous solution because of the stable voltage at interfaces of Ag-AgCl and AgCl-KCl through fast charge-transfer steps, regardless of the magnitude of current density. The “fast step” means the absence of delay of the reaction or being in a quasi-equilibrium. The stability without delay is supported with high concentration of KCl.
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When an Ag-AgCl electrode is inserted to a voltammetric solution, KCl necessarily diffuses into the solution, associated with oxygen from the reference electrode. Thus, the reference electrode is a source of contamination by salt, dichlorosilver and oxygen. It is interesting to examine how much amount a solution is contaminated by a reference electrode [9]. Time variation of ionic conductivity in the pure water was monitored immediately after a commercially available Ag-AgCl electrode was inserted into the solution. Figure 6 shows rapid increase in the conductivity as if a solid of KCl was added to the solution. Oxygen included in the concentrated KCl may contaminate a test solution. Even the Ag-AgxO electrode, which was formed by oxidizing silver wire, increased also the conductivity, probably because the surface is in the form of silver hydroxide. As a result, no reference electrode can be used for studying salt-free electrode reactions. If neutral redox species such as ferrocene is included in a solution, the potential reference can be taken from redox potential of ferrocene.
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Figure 6.
Time-variation of conductivity of water into which (circles) Ag|AgCl, (triangles) Ag|AgxO, and (squares) AgCl-coated Ag wire were inserted. Conductivity measurement was under N2 environment.
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3.9. Current flowing through the double layer
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When a constant voltage is applied to the ideal capacitance C, the responding current decays in the form of exp(−t/RC), where R is a resistance in series connected with C. It has been believed that a double-layer capacitance in electrochemical system behaves as an ideal capacitor, where R is regarded as solution resistance. However, any exponential variation cannot reproduce transient currents obtained at the platinum wire electrode in KCl aqueous solution, as shown in Figure 7. The current decays more slowly than by exp(−t/RC), because it is approximately proportional to 1/t. The property of non-ideal capacitance is the result of the constant phase element of the DL capacitance, as described in Section 2.3. The dependence of 1/t can be obtained approximately by the time derivative of q = V0C0t−λ for the voltage step V0.
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Figure 7.
Chronoamperometric curves when 0.2 V vs. Ag|AgCl was applied to a Pt wire in 0.5 M KCl aqueous solution. Solid curves are fitted ones by exp(-t/RC) for three values of RC.
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The slow decay is related with a loss of the performance of pulse voltammetry, in which diffusion-controlled currents can readily be excluded from capacitive currents. The advantage of pulse voltammetry is based on the assumption of the exponential decay of the capacitive current. Since the diffusion current with 1/t1/2 dependence is close to the 1/t dependence, it cannot readily be separated from the capacitive current in reality. A key of using pulse voltammetry is to take a pulse time to be so long as a textbook recommends.
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High-performance potentiostats are equipped with a circuit for compensation of resistance by a positive feedback. Unfortunately, the circuit is merely useful because voltammograms depend on intensity of compensation resistances of the DL capacitance. It should work well if the DL capacitance is ideal.
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3.10. Advantages of AC impedance
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AC techniques have an advantage of examining time dependence at a given potential, whereas CV has a feature of finding current-voltage curves at a given time. The former shows the dynamic range from 1 Hz to 10 kHz, while the latter does conventionally from 0.01 to 1 Hz. This wide dynamic range of the AC technique is powerful for examining dynamics of electrode reactions. Analytical results by the former are often inconsistent with those by the latter, because of the difference in the time domain. The other scientific advantage of the AC technique is to get two types of independent data set, frequency variations of real components and imaginary ones by the use of a lock-in amplification. The independence allows us to operate mathematically the two data, leading to the data analysis at a level one step higher than CV. An industrial advantage is the rapid measurement, which can be applied to quality control for a number of samples. The analysis of AC impedance necessarily needs equivalent circuits of which components do not have any direction relation with electrochemical variables.
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Data of the electrochemical AC impedance are represented by Nyquist (Cole-Cole) plots, that is, plots of the imaginary component (Z2) of the impedance against the real one (Z1), as shown in Figure 8. The simplest equivalent circuit for electrochemical systems is the DL capacitance Cd in series with the solution resistance RS. The Nyquist plot for this series circuit is theoretically parallel to the vertical axis (Figure 8A-a), but experiments show a slope of 5 or more (Figure 8A-b). This behavior, called constant phase element (CPE) and the power law, has been verified for combinations of various materials and solvents [6, 7, 11, 12]. The equivalent circuit for Eq. (12) is a parallel combination of capacitance and resistance (Figure 8B). Even without an electrode reaction, current always includes a real component.
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Figure 8.
(A) Nyquist plots for a RC-series circuit with ideal capacitor (a) and DL capacitor (b). (B) Equivalent circuit with the power-law of Cd. (C) Randles circuit.
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The equivalent circuit with the Randles type is a parallel combination of the ideal DL capacitor Cd with the ideal resistance Rct representing the Butler-Volmer-type charge-transfer resistance. Practically, the Warburg impedance (the inverse of Eq. (8)) due to diffusion of redox species is incorporated in a series into Rct (Figure 8C). Rct cannot be separated from the DL resistance because of the frequency dispersion. Since even the existence of Rct is in question (Section 3.12), it is difficult to determine and interpret Rct. The usage of a software that can analyze any Nyquist plots will provide values of R and C. Even if analyzed values are in high accuracy, researches should give them electrochemical significance.
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3.11. Residual currents depending on surface treatments
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Residual current varies with treatments of electrodes such as polishing of electrode surfaces and voltage applications to an extremely high domain. It can often be suppressed to yield reproducible data when the electrode is replaced by simple platinum wire or carbon rod having the same geometric area. Simple wire electrodes are quite useful especially for measurements of DL capacitance and adsorption. One of the reasons for setting off large residual current is that the insulator of confining the active area is not in close contact with the electrode, so that the solution penetrated into the gap will give rise to capacitive current and floating electrode reactions. Since the coefficient of thermal expansion of the electrode is different from that of the insulator, the residual current tends to get large with the elapse from the fabrication of the electrode. This prediction is based on experience, and there are few quantitative studies on residual currents.
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Unexpected gap has been a technical problem at dropping mercury electrodes. If solution penetrates the inner wall of the glass capillary containing mercury, observed currents become irreproducible. Water repellency of the capillary tip has been known to improve the irreproducibility in order to reduce the penetration. A similar technique has been used for voltammetry at oil-water interfaces and ionic liquid-water interfaces at present.
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3.12. Reversible or irreversible voltammograms
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Voltammograms are said to vary with electrode reaction rates, and the rate constants have been determined from time dependence of voltammograms. The fast reaction of which rate is not rate determining has historically been called “reversible.” In contrast, such a slow reaction that a peak potential varies linearly with log v is called “irreversible.” A reaction between them is called “quasi-reversible.” The distinction among the three has been well known since the theoretical report on the quasi-reversible reaction by Matsuda [1]. This theory is devoted to solving the diffusion equations with boundary conditions of the Butler-Volmer (BV) equation under the potential sweep. As the standard rate constant ks in the BV equation becomes small, the peak shifts in the direction of the potential sweep from the diffusion-controlled peak. Steady-state current-potential curves in a microelectrode [13] and a rotating disk electrode also shift the potential in a similar way. According to the calculated CV voltammograms in Figure 9, we can present some characteristics: (i) if the oxidation wave shifts to the positive potential, the negative potential shift should also be found in the reduction wave. (ii) Both the amounts of the shift should have a linear relationship to log v. (iii) The shift should be found in iterative measurements. (iv) The peak current should be proportional to v1/2.
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Figure 9.
CV voltammograms (solid curves) at a normally sized electrode and steady-state voltammograms (dashed curves) at a microelectrodes in 12 μm in diameter, calculated theoretically for v = 0.5 V s−1, D = 0.73 × 10−5 cm2 s−1, ks = (a) 0.1, (b) 0.01, (c) 0.001, (d) 0.0001 cm s−1. The potential shift of CV is equivalent to the wave-shift at a microelectrode through the relation, v = 0.4RTD/αFa2 (a: radius).
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The authors attempted to find a redox species with the above four behaviors. Some redox species can satisfy one of the four requirements, but do not meet the others. Most reaction rate constants have been determined from the potential shift in a narrow time domain. They are probably caused by follow-up chemical reactions, adsorption, or DL capacitance. For example, CV peak potentials of TCNQ and benzoquinone were shifted at high scan rates, whereas their steady-state voltammograms were independent of diameters of microdisk electrodes even on the nanometer scale [14]. The shift at high scan rates should be due to the frequency dispersion of the DL capacitance, especially the parallel resistance in the DL (Figure 8B). Values of the heterogeneous rate constants and transfer coefficients reported so far have depended not only on the electrochemical techniques but also research groups. Furthermore, they have not been applied or extended to next developing work. These facts inspire us to examine the assumptions and validity of the BV formula.
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Let us revisit the assumptions of the BV equation when an overvoltage, i.e., the difference of the applied potential from the standard electrode potential, causes the electrode reaction. The rate of the oxidation in the BV equation is assumed to have the activation energy of α times the overvoltage, while that of the reduction does that of (1 − α) times. This assumption seems reasonable for the balance of both the oxidation and the reduction. However, the following two points should be considered. (i) Once a charge or an electron is transferred within the redox species, the molecular structure changes more slowly than the charge transfer itself occurs. The structure change causes solvation as well as motion of external ions to keep electric neutrality. These processes should be slower than the structure change. If the overvoltage can control the reaction rate, it should act on to the slowest step, which is not the genuine charge-transfer process. (ii) Since a reaction rate belongs to the probability theory, the reaction rate (dc/dt) at t is determined with the state at t rather than a state in the future. In other words, the rate of the reduction should have no relation with the oxidation state which belongs to the future state. The BV theory assumes that the α times activation energy for the oxidation is related closely with 1-α times one for the reduction. This assumption is equivalent to predicting a state at t + Δt from state at t + 2Δt, like riding on a time machine. This question should be solved from a viewpoint of statistical physics.
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3.13. Contradiction of microscopic image with electrochemical data
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Development of scanning microscopes such as STM and AFM has allowed us to obtain the molecularly and atomically regulated surface images, which have been used for interpreting electrochemical data. Then the electrochemical data are expected to be discussed on a molecular scale. However, there is an essential problem of applying photographs of regularly arranged atoms on an electrode to electrochemical data, because the former and the latter include, respectively, microscopically local information and macroscopically averaged one. A STM image showing molecular patterns is information of only a part of electrode, at next parts of which no atomic images are often observed but noisy images are found. Electrochemical data should be composed of information both at a part of the electrode showing the molecular patters and at other parts showing noisy, vague images. Noisy photographs are always discarded for interpreting electrochemical data although the surfaces with noisy images also contribute electrochemical data.
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An ideal experiment would be made by taking STM images over all the electrodes that provide electrochemical data and by obtaining an averaged image. However, it is not only impossible to take huge amounts of images, but the averaged image might be also noisy. It may be helpful to describe only a possibility of reflecting the STM-imaged atomic structure on the electrochemical data.
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3.14. Surface wave by adsorption
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Voltammograms by adsorbed redox species, called surface waves, are frequently different from a bell shape (Figure 2). Really observed features are the following: (i) the voltammogram does not suddenly decay after the peak, exhibiting a tail-like diffusional wave; (ii) the peak current and the amount of the electricity are proportional to the power less than the unity of v; (iii) the oxidation peak potential is different from the reduction one; (iv) the background current cannot be determined unequivocally; and (v) voltammograms depend on the starting potential. Why are experimental surface waves different from a symmetric, bell shape in Figure 2?
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A loss of the symmetry with respect to the vertical line passing through a peak can be ascribed to the difference in interactions at the oxidized potential domain and at the reduced one. Since redox species takes extremely high concentration in the adsorbed layer, interaction is highly influenced on voltammetric form. When the left-right asymmetry is ascribed to thermodynamic interaction, it has been interpreted not only with Frumkin’s interaction [15] but also Bragg-Williams-like model for the nearest neighboring interactive redox species [16]. On the other hand, most surface waves are asymmetric with respect to the voltage axis even at extremely slow scan rates. This asymmetry cannot be explained in terms of thermodynamics of intermolecular interaction, but should resort to kinetics or a delay of electrode reactions. There seems to be no delay in the electrode reaction of the monomolecular adsorption layer, different from diffusion species. The delay resembles the phenomenon of constant phase element (CPE) or frequency power law of DL capacitance, in that the redox interaction may occur two-dimensionally so that the most stable state can be attained. This behavior belongs to a cooperative phenomenon [17]. A technique of overcoming these complications is to discuss the amount of charge by evaluating the area of the voltammogram. It also includes ambiguity of eliminating background current and assuming the independence of the redox charge from the DL charge.
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4. Conclusions
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The simplest theories for voltammetry are limited to the rate-determining steps of diffusion of redox species and reactions of adsorbed species without interaction. Variation of scan rates as well as a reverse potential is helpful for predicting redox species and reaction mechanisms. Furthermore, the following viewpoints are useful for interpreting mechanisms:
comparison of values of experimental peak currents with theoretical ones, instead of discussing ΔEp and E1/2;
examining the proportionality of Ip vs. v or vs. v1/2, i.e., zero or non-zero values of the intercept of the linearity;
a reference electrode and a counter electrode being a source of contamination in solution;
attention to very slow relaxation of DL capacitive currents;
inclusion of ambiguity in the equivalent circuit with the Randles type.
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\n\n',keywords:"current-voltage curves, cyclic voltammetry, AC impedance, double-layer capacitance, diffusion control, surface wave",chapterPDFUrl:"https://cdn.intechopen.com/pdfs/63917.pdf",chapterXML:"https://mts.intechopen.com/source/xml/63917.xml",downloadPdfUrl:"/chapter/pdf-download/63917",previewPdfUrl:"/chapter/pdf-preview/63917",totalDownloads:1597,totalViews:467,totalCrossrefCites:1,dateSubmitted:"June 15th 2018",dateReviewed:"September 5th 2018",datePrePublished:"November 5th 2018",datePublished:null,dateFinished:null,readingETA:"0",abstract:"Theories of cyclic voltammetry, AC-impedance techniques, and the double-layer capacitive currents are described concisely to touch their principles. Applications of the theory to experimental data do not always lead to reasonable interpretation consistent with other techniques. Several tips are presented not only in the experimental viewpoint but also in a perspective of the data analysis. Most of them are devoted to cyclic voltammetry. They include shape of voltammograms, information from peak currents and peak potentials, criteria of diffusion and adsorption controls, the static and the dynamic numbers of electrons, handling of reference and counter electrodes, usage of AC impedance, concepts of heterogeneous charge-transfer rates, and combination with data by scanning probe microscope. They belong partially to recommendation and prohibition.",reviewType:"peer-reviewed",bibtexUrl:"/chapter/bibtex/63917",risUrl:"/chapter/ris/63917",signatures:"Koichi Jeremiah Aoki and Jingyuan Chen",book:{id:"7348",title:"Voltammetry",subtitle:null,fullTitle:"Voltammetry",slug:"voltammetry",publishedDate:"June 12th 2019",bookSignature:"Nobanathi Wendy Maxakato, Sandile Surprise Gwebu and Gugu Hlengiwe Mhlongo",coverURL:"https://cdn.intechopen.com/books/images_new/7348.jpg",licenceType:"CC BY 3.0",editedByType:"Edited by",editors:[{id:"259515",title:"Dr.",name:"Nobanathi Wendy",middleName:null,surname:"Maxakato",slug:"nobanathi-wendy-maxakato",fullName:"Nobanathi Wendy Maxakato"}],productType:{id:"1",title:"Edited Volume",chapterContentType:"chapter",authoredCaption:"Edited by"}},authors:[{id:"263291",title:"Prof.",name:"Koichi",middleName:"Jeremiah",surname:"Aoki",fullName:"Koichi Aoki",slug:"koichi-aoki",email:"kaoki@u-fukui.ac.jp",position:null,institution:{name:"University of Fukui",institutionURL:null,country:{name:"Japan"}}},{id:"263292",title:"Prof.",name:"Jingyuan",middleName:null,surname:"Chen",fullName:"Jingyuan Chen",slug:"jingyuan-chen",email:"jchen@u-fukui.ac.jp",position:null,institution:{name:"University of Fukui",institutionURL:null,country:{name:"Japan"}}}],sections:[{id:"sec_1",title:"1. Introduction",level:"1"},{id:"sec_2",title:"2. Theory",level:"1"},{id:"sec_2_2",title:"2.1. Diffusion-controlled current",level:"2"},{id:"sec_2_3",title:"2.1.1. Linear sweep voltammetry by diffusion",level:"3"},{id:"sec_3_3",title:"2.1.2. AC voltammetry by diffusion",level:"3"},{id:"sec_5_2",title:"2.2. Adsorption-controlled current",level:"2"},{id:"sec_5_3",title:"2.2.1. Linear sweep voltammetry by adsorption",level:"3"},{id:"sec_7_2",title:"2.3. Capacitive current",level:"2"},{id:"sec_7_3",title:"2.3.1. Capacitance by AC impedance",level:"3"},{id:"sec_8_3",title:"2.3.2. Capacitive current by CV",level:"3"},{id:"sec_11",title:"3. Tips of voltammetric analysis",level:"1"},{id:"sec_11_2",title:"3.1. Understanding outline of voltammograms",level:"2"},{id:"sec_12_2",title:"3.2. Shape and values of peaks",level:"2"},{id:"sec_13_2",title:"3.3. Deviation of ΔEp from theoretical values",level:"2"},{id:"sec_14_2",title:"3.4. 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Zeitschrift für Elektrochemie. 1955;59:494-503\n'},{id:"B2",body:'Barsoukov E, Macdonald JR. Impedance Spectroscopy. New York: Wiley; 2005. ISBN: 0-471-64749-7\n'},{id:"B3",body:'Lasia A. In: White RE, Conway BE, Bockris JO’M, editors. Modern Aspects of Electrochemistry. Vol. 32. New York: Kluwer Academic/Plenum Publishers; 1999. pp. 143-248\n'},{id:"B4",body:'Brug GJ, Van Den Eeden ALG, Sluyters-Rehbach M, Sluyters JH. The analysis of electrode impedances complicated by the presence of a constant phase element. Journal of Electroanalytical Chemistry. 1984;176:275-295. DOI: 10.1016/S0022-0728(84)80324-1\n'},{id:"B5",body:'Zoltowski P. On the electrical capacitance of interfaces exhibiting constant phase element behaviour. Journal of Electroanalytical Chemistry. 1998;443:149-154. DOI: 10.1016/S0022-0728(97)00490-7\n'},{id:"B6",body:'Hou Y, Aoki KJ, Chen J, Nishiumi T. Invariance of double layer capacitance to polarized potential in halide solutions. 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DOI: 10.1002/ange.19680800321\n'},{id:"B11",body:'Aoki KJ, Wang H, Chen J, Nishiumi T. Formation of graphite oxide nano-disks by electrochemical oxidation of HOPG. Electrochimica Acta. 2014;130:381-386. DOI: 10.1016/j.electacta.2014.03.044\n'},{id:"B12",body:'Wang H, Aoki KJ, Chen J, Nishiumi T, Zeng Z, Ma X. Power law for frequency-dependence of double layer capacitance of graphene flakes. Journal of Electroanalytical Chemistry. 2015;741:114-119. DOI: 10.1016/j.jelechem.2015.01.008\n'},{id:"B13",body:'Aoki K. Evaluation technique of kinetic parameters for irreversible charge transfer reactions from steady-state voltammograms at microdisk electrodes. Electrochemistry Communications. 2005;17:523-527. DOI: 10.1016/j.elecom.2005.03.006\n'},{id:"B14",body:'Aoki KJ, Zhang C, Chen J, Nishiumi T. Heterogeneous reaction rate constants by steady-state microelectrode techniques and fast scan voltammetry. Journal of Electroanalytical Chemistry. 2013;706:40-47. DOI: 10.1016/j.jelechem.2013.07.021\n'},{id:"B15",body:'Bard AJ, Faulkner LR. Electrochemical Methods: Fundamentals and Applications. 2nd ed. New York, NY: John Wiley & Sons; 2001. p. 567. ISBN: 0-471-04372-9\n'},{id:"B16",body:'example F, Aoki K, Chen J. Statistical thermodynamics of multi-nuclear linear complexes with mixed valence states by means of correlated-walk. Journal of Electroanalytical Chemistry. 1995;380:35-45. DOI: 10.1016/0022-0728(94)03603-Z\n'},{id:"B17",body:'Aoki KJ. Molecular interaction model for frequency-dependence of double layer capacitors. Electrochimica Acta. 2016;188:545-550. DOI: 10.1016/j.electacta.2015.12.049\n'}],footnotes:[],contributors:[{corresp:"yes",contributorFullName:"Koichi Jeremiah Aoki",address:"kaoki@u-fukui.ac.jp",affiliation:'
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Open Access publication costs can often be designated directly in the grants or in specific budgets allocated for that purpose. Many of the most important funding organisations encourage, and even request, that the projects they fund are made available at no cost to the wider public. IntechOpen strives to maintain excellent relationships with these funders and ensures compliance with mandates.
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