Making and Exploiting Fullerenes, Graphene, and Carbon Nanotubes PDF
Preview Making and Exploiting Fullerenes, Graphene, and Carbon Nanotubes
Topics in Current Chemistry 348 Massimo Marcaccio Francesco Paolucci Editors Making and Exploiting Fullerenes, Graphene, and Carbon Nanotubes 348 Topics in Current Chemistry EditorialBoard: H.Bayley,Oxford,UK K.N.Houk,LosAngeles,CA,USA G.Hughes,CA,USA C.A.Hunter,Sheffield,UK K.Ishihara,Chikusa,Japan M.J.Krische,Austin,TX,USA J.-M.Lehn,StrasbourgCedex,France R.Luque,Co´rdoba,Spain M.Olivucci,Siena,Italy J.S.Siegel,NankaiDistrict,China J.Thiem,Hamburg,Germany M.Venturi,Bologna,Italy C.-H.Wong,Taipei,Taiwan H.N.C.Wong,Shatin,HongKong Aims and Scope TheseriesTopicsinCurrentChemistry presentscriticalreviews ofthepresent and futuretrendsinmodernchemicalresearch.Thescopeofcoverageincludesallareasof chemical science including the interfaces with related disciplines such as biology, medicineandmaterialsscience. Thegoalofeachthematicvolumeistogivethenon-specialistreader,whetherat theuniversityorinindustry,acomprehensiveoverviewofanareawherenewinsights areemergingthatareofinteresttolargerscientificaudience. Thuseachreviewwithinthevolumecriticallysurveysoneaspectofthattopicand placesitwithinthecontextofthevolumeasawhole.Themostsignificantdevelop- mentsofthelast5to10yearsshouldbepresented.Adescriptionofthelaboratory procedures involved is often useful to the reader. The coverage should not be exhaustiveindata,butshouldratherbeconceptual,concentratingonthemethodolog- icalthinkingthatwill allowthenon-specialistreaderto understandtheinformation presented. Discussionofpossiblefutureresearchdirectionsintheareaiswelcome. Reviewarticlesfortheindividualvolumesareinvitedbythevolumeeditors. Readership:researchchemistsatuniversitiesorinindustry,graduatestudents. Moreinformationaboutthisseriesat http://www.springer.com/series/128 Massimo Marcaccio Francesco Paolucci l Editors Making and Exploiting Fullerenes, Graphene, and Carbon Nanotubes With contributions by (cid:1) (cid:1) (cid:1) (cid:1) P. Bachawala L. Ballerini M. Bonchio S. Bosi (cid:1) (cid:1) (cid:1) E. Cadelano S. Campidelli L. Colombo (cid:1) (cid:1) (cid:1) C. Degli Esposti Boschi F. D’Souza A. Filoramo (cid:1) (cid:1) (cid:1) (cid:1) P. Fornasiero G. Gavrel D.R. Jones B. Jousselme (cid:1) (cid:1) (cid:1) (cid:1) L. Kavan W. Kutner J. Mack A. Mateo-Alonso (cid:1) (cid:1) (cid:1) (cid:1) M. Melchionna A. Migliori V. Morandi L. Ortolani F. Paolucci (cid:1) A. Pe´nicaud (cid:1) M. Prato (cid:1) P.S. Sharma Editors MassimoMarcaccio FrancescoPaolucci Dept.ofChemistryG.Ciamician UniversityofBologna Bologna Italy ISSN0340-1022 ISSN1436-5049(electronic) ISBN978-3-642-55082-9 ISBN978-3-642-55083-6(eBook) DOI10.1007/978-3-642-55083-6 SpringerHeidelbergNewYorkDordrechtLondon LibraryofCongressControlNumber:2014947108 #Springer-VerlagBerlinHeidelberg2014 Thisworkissubjecttocopyright.AllrightsarereservedbythePublisher,whetherthewholeorpartof the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation,broadcasting,reproductiononmicrofilmsorinanyotherphysicalway,andtransmissionor informationstorageandretrieval,electronicadaptation,computersoftware,orbysimilarordissimilar methodologynowknownorhereafterdeveloped.Exemptedfromthislegalreservationarebriefexcerpts inconnectionwithreviewsorscholarlyanalysisormaterialsuppliedspecificallyforthepurposeofbeing enteredandexecutedonacomputersystem,forexclusiveusebythepurchaserofthework.Duplication ofthispublicationorpartsthereofispermittedonlyundertheprovisionsoftheCopyrightLawofthe Publisher’s location, in its current version, and permission for use must always be obtained from Springer.PermissionsforusemaybeobtainedthroughRightsLinkattheCopyrightClearanceCenter. ViolationsareliabletoprosecutionundertherespectiveCopyrightLaw. The use of general descriptive names, registered names, trademarks, service marks, etc. in this publicationdoesnotimply,evenintheabsenceofaspecificstatement,thatsuchnamesareexempt fromtherelevantprotectivelawsandregulationsandthereforefreeforgeneraluse. While the advice and information in this book are believed to be true and accurate at the date of publication,neithertheauthorsnortheeditorsnorthepublishercanacceptanylegalresponsibilityfor anyerrorsoromissionsthatmaybemade.Thepublishermakesnowarranty,expressorimplied,with respecttothematerialcontainedherein. Printedonacid-freepaper SpringerispartofSpringerScience+BusinessMedia(www.springer.com) Preface Carbon nanostructures, or nanocarbons (CNSs), i.e. the low-dimensional nanoma- terialsthatcomprise0Dfullerenes,1Dnanotubesand2Dgraphene,haveemerged over the last two decades in the field of new molecular materials for their unique structuralandelectronicproperties,promptingahugeinterestworldwidebothfrom the viewpointof fundamental research and for their application in molecular elec- tronics,materialsscience,energystorageandconversion,biomedicine,sensingand biosensing. The electronic properties of CNSs and their optical, spectroscopic and electrochemical behaviour depend markedly on their characteristic nanometric dimensions;theidentificationofspecificquantitiesrelativetoindividualnanostruc- turesinthebulkphasehasprovedchallengingandhasrequiredextremeingenuity. Making solutions (or suspensions) of CNSs where the nanostructures could retain most of their pristine properties has been a prerequisite for either fundamental investigation or for the development of any viable technological exploitation of such properties. This was the case, for example, of the application of bandgap fluorescence spectroscopy of aqueous, micelle-like suspensions of single-walled carbon nanotubes (SWNTs) that has given access to the electronic energies of individualsemiconductingSWNTsasafunctionofstructurediameterandhelicity. Insuchacontext,thechapter“SolubilizationofFullerenes,CarbonNanotubesand Graphene” by AlainPe´nicauddescribes thevarious ingeniousapproaches tosolve the solubility issue and describes in particular how graphite, and modern nanocar- bons, can be made soluble by reductive dissolution. A large part of the present volumeconcernsthemergingofnanocarbonswithnanotechnologyandtheirimpact on technical development in many areas. Fullerenes, carbon nanotubes, nanodia- mond and graphene find, for instance, various applications in the development of solarcells,includingdyesensitizedsolarcells.Thechapter“IncorporationofBalls, TubesandBowlsinNanotechnology”byJamesMackdescribestherecentdevelop- ment of the area of fullerene fragments, and corannulene in particular, and their directapplicationstoorganiclightemittingdiode(OLED)technology,while,inthe chapter“ExploitingNanocarbonsinDye-SensitizedSolarCells”byLadislavKavan, the exploitation of nanocarbons in the development of novel dye sensitized solar cellswithimprovedefficiency,durabilityandcostsisthoroughlyreviewed. v vi Preface ThefunctionalizationofCNSshastheinvaluableadvantageofcombiningtheir uniquepropertieswiththoseofotherclassesofmaterials.Supramolecularchemis- try represents an elegant alternative approach for the construction of functional systems by means of noncovalent bonding interactions. In the chapter “Supramo- lecular Chemistry of Carbon Nanotubes” by Gildas Gavrel et al., the incredibly varied world of supramolecular, non-covalent functionalization of carbon nano- tubesandtheirapplicationsisexaminedandreviewed,andthesyntheticstrategies devised for fabricating mechanically-linked molecular architectures are described inthechapter“Fullerene-StopperedBistableRotaxanes”byAurelioMateo-Alonso, which presents an overview of the different types of fullerene-stoppered bistable rotaxanes,theirswitchingmechanismandtheirpotentialapplications. Inthechapter“Catalysis-MaterialCrosstalkatTailoredNano-CarbonInterfaces” by Michele Melchionna et al., carbon nanomaterials are described as supports for molecular and nanostructured catalysts, where their outstanding electronic and opticalproperties,highsurfaceareaandthermalandmechanicalstabilitycontribute tocreateasynergisticeffectthatleadstoenhancedperformanceforawiderangeof possibleapplications.Exploitationofnanocarbonsinbiologyandbiomedicalappli- cations has been increasingly proposed and, in particular, the chapter “Carbon Nanotubes in Tissue Engineering” by Susanna Bosi et al. explores applications of CNTsfortissueengineeringpurposes,wherethetubesprovedtobeidealmaterials forthegrowthandproliferationofmanykindoftissues. Thelocalchemicalreactivity,themechanicalpropertiesandtheelectrontransfer ingraphenemembraneshavebeenshowntobestronglyaffectedbythefold-induced curvature; thus in the chapter “Folds and Buckles at the Nanoscale: Experimental andTheoreticalInvestigationoftheBendingPropertiesofGrapheneMembranes”by Vittorio Morandi, a novel methodologytoinvestigate the mechanicalpropertiesof foldedandwrinkledgraphenecrystals,whichcombinetransmissionelectronmicros- copymappingandtheoreticalmodelling,isdescribed.Grapheneandnanocarbonsin general are intensively investigated as platforms for the development of sensing devicesfortheselectiveandhighlysensitivedetectionofbiohazards.Theaimofthe chapter “Graphene and Graphene Oxide Materials for Chemo- and Biosensing of ChemicalandBiochemicalHazards”byPiyushSindhuSharmaetal.isthentobring out important advances of graphene-based sensors, with particular attention to the rapiddetectionandquantizationoftoxins,explosives,pesticidesandpathogens. Becauseoftheseveralanddiversetechnologicalapplicationssofarproposed,and of the many more expected in the near future, the present volume is addressed to researchersfromseveraldifferentareas:chemistryandmaterialschemistry,nanotech- nology,medicineandindustrialresearch.Wehopetheywillenjoythepresentations andfindinspirationfortheirresearchactivityinthefascinatingfieldofnanocarbons. Finally,we would liketo thank Prof. MargheritaVenturiwho, as amemberof theEditorialBoardofTopicsinCurrentChemistry,promotedthepreparationofa volumeonthissubject. Bologna,Italy MassimoMarcaccio November2013 FrancescoPaolucci Contents SolubilizationofFullerenes,CarbonNanotubes,andGraphene ........... 1 AlainPe´nicaud IncorporationofBalls,Tubes,andBowlsinNanotechnology ............. 37 DerekR.Jones,PraveenBachawala,andJamesMack ExploitingNanocarbonsinDye-SensitizedSolarCells ..................... 53 LadislavKavan SupramolecularChemistryofCarbonNanotubes ......................... 95 GildasGavrel,BrunoJousselme,AriannaFiloramo,andSte´phaneCampidelli Fullerene-StopperedBistableRotaxanes ................................... 127 AurelioMateo-Alonso Catalysis-MaterialCrosstalkatTailoredNano-CarbonInterfaces ...... 139 MicheleMelchionna,MarcellaBonchio,FrancescoPaolucci, MaurizioPrato,andPaoloFornasiero CarbonNanotubesinTissueEngineering .................................. 181 SusannaBosi,LauraBallerini,andMaurizioPrato FoldsandBucklesattheNanoscale:ExperimentalandTheoretical InvestigationoftheBendingPropertiesofGrapheneMembranes ...... 205 VittorioMorandi,LucaOrtolani,AndreaMigliori, CristianDegliEspostiBoschi,EmilianoCadelano,andLucianoColombo GrapheneandGrapheneOxideMaterialsforChemo-andBiosensing ofChemicalandBiochemicalHazards ..................................... 237 PiyushSindhuSharma,FrancisD’Souza,andWlodzimierzKutner Index .......................................................................... 267 vii TopCurrChem(2014)348:1–36 DOI:10.1007/128_2013_520 #Springer-VerlagBerlinHeidelberg2014 Publishedonline:20March2014 Solubilization of Fullerenes, Carbon Nanotubes, and Graphene AlainPe´nicaud Abstract Processing of novel carbon forms, i.e. fullerenes, nanotubes and graphene,insolutionisdescribed.C andhigherfullerenesappeartobetheonly 60 trulysolubleformsofpurecarbon.Waystodispersecarbonnanotubesandgraphene arereviewed.Truesolutionsofcarbonnanotubesandgraphenecanbeobtainedby reductive dissolution, leading to solution of polyelectrolyte nanocarbons of high concentrations without damaging the nanocarbon. Finally it is shown that these solutions allow to obtain high performing materials such as highly conducting transparentelectrodes. Keywords C (cid:1) Carbon (cid:1) Dissolution (cid:1) Entropy (cid:1) Fullerenes (cid:1) GIC (cid:1) Graphene (cid:1) 60 Graphenide (cid:1) Graphite (cid:1) Individualization (cid:1) Nanotube salts (cid:1) Nanotubes (cid:1) Nanotubide(cid:1)Solutions Contents 1 Introduction................................................................................. 2 1.1 SizeIsImportant...................................................................... 3 2 FromDiamondandGraphitetoNanocarbonsorNanocarbonSizeVsSolubility....... 4 2.1 SomeNomenclature.................................................................. 4 3 TheSpecialCaseofC .................................................................... 5 60 4 StrategiestoDisperseCarbonNanotubes.................................................. 9 4.1 DispersionsinOrganicSolvents..................................................... 10 4.2 AqueousSuspensions................................................................. 11 5 ReductiveDissolutionofNanotubes....................................................... 11 5.1 SynthesisofNanotubeSalts.......................................................... 12 5.2 Individualization...................................................................... 13 5.3 DissolutionMechanism............................................................... 15 5.4 MultiwalledNanotubes............................................................... 17 A.Pe´nicaud(*) CNRS,CentredeRecherchePaulPascal(CRPP),Universite´deBordeaux,UPR8641, Pessac33600,France e-mail:[email protected] 2 A.Pe´nicaud 5.5 ReducedNanotubesforFunctionalization........................................... 17 5.6 SortingNanotubes.................................................................... 19 5.7 ElectrochemicalSynthesis............................................................ 20 6 GraphenideSolutions....................................................................... 20 7 NanoconesDissolution..................................................................... 25 7.1 CarbonNanocones.................................................................... 25 8 OxidativeDissolutionofNanocarbons..................................................... 27 9 ApplicationsandMaterialsfromNanocarbideSolutions................................. 28 9.1 Cryogels............................................................................... 28 9.2 FieldEffectTransistors............................................................... 29 9.3 Catalysts............................................................................... 29 9.4 TransparentConductingFilms....................................................... 29 10 ConclusionandPerspectives............................................................... 30 References........................................................................................ 31 Abbreviations AFM Atomicforcemicroscopy CNT Carbonnanotube CoMoCAT ProcessinwhichcarbonnanotubesaresynthesizedwithCo/Mo catalysts DMSO Dimethylsulfoxide GIC Graphiteintercalationcompound GO Grapheneoxide HiPCO Highpressurecarbonmonoxideprocesstosynthesizecarbon nanotubes HOPG Highlyorderedpyrolyticgraphene NMP N-Methylpyrrolidone PAH Polyaromatichydrocarbon RGO Reducedgrapheneoxide SCE Standardcalomelelectrode SEM Scanningelectronmicroscopy SWCNT Single-wallcarbonnanotube TEM Transmissionelectronspectroscopy THF Tetrahydrofuran 1 Introduction Excluding metallic elements, carbon is one of the few elements of the Periodic Tablethathasledtomanyfundamentallyimportantmaterials.Unlikemetals,carbon exhibitsavarietyofvalencetopology,dependingonitshybridizationsp,sp2,orsp3, and even intermediate hybridization. This has led to an amazing variety of nature, appearance, and properties within carbon materials. Let’s mention graphite and diamond, the former opaque, slippery, and conducting, the latter transparent, hard, andinsulating.Importantcarbonmaterialsarenotrestrictedtographiteanddiamond.
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