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Editedby ChunyingChenand HaifangWang BiomedicalApplicationsandToxicology ofCarbonNanomaterials RelatedTitles Stanley,L.A. HandbookofSystems MolecularandCellular Toxicology2VSet Toxicology-AnIntroduction 2011 2013 PrintISBN:978-0-470-68401-6 PrintISBN:978-1-119-95207-7 ePubISBN:978-1-118-52601-9 Syversen,T.T.(ed.) AdobePDFISBN:978-1-118-52606-4 CourseSmartISBN:978-1-118-87137-9 GeneralandApplied VitaleBookPDFISBN:978-1-118-87152-2 Toxicology3e6Vset Braithwaite,R.R.(ed.) 2009 AppliedToxicology PrintISBN:978-0-470-72327-2 ISBN:978-0-470-74430-7 –AnalyticalAspectsofForensic andClinicalToxicology Nanotoxicity –FromInVivo 2016 PrintISBN:978-1-119-95232-9 andInVitroModelstoHealth ePubISBN:978-1-118-68353-8 Risks WOLobookPDFISBN:978-1-118-68363-7 AdobePDFISBN:978-1-118-68370-5 2009 PrintISBN:978-0-470-74137-5 AdobePDFISBN:978-0-470-74779-7 EnvironmentalandHuman ISBN:978-0-470-74780-3 HealthImpactsof Nanotechnology Nanotoxicity –FromInVivo 2009 andInVitroModelstoHealth PrintISBN:978-1-444-30750-4 Risks Vogel,V.(ed.) 2009 PrintISBN:978-0-470-74780-3 Nanotechnology Volume5:Nanomedicine 2009 PrintISBN:978-3-527-31736-3 Mumtaz,M.(ed.) Zhao,Y.,Shen,Y.(eds.) PrinciplesandPracticeof BiomedicalNanomaterials MixturesToxicology 2016 2010 PrintISBN:978-3-527-33798-9 PrintISBN:978-3-527-31992-3 WOLobookPDFISBN:978-3-527-69439-6 ISBN:978-3-527-63019-6 ePubISBN:978-3-527-69441-9 AdobePDFISBN:978-3-527-63020-2 MobiPocketISBN:978-3-527-69442-6 ePubISBN:978-3-527-63211-4 AdobePDFISBN:978-3-527-69443-3 MobiPocketISBN:978-3-527-64039-3 Zhang,Z.,Feng,W.,Zhao,Y.(eds.) ToxicologyofNanomaterials 2016 PrintISBN:978-3-527-33797-2 WOLobookPDFISBN:978-3-527-68912-5 AdobePDFISBN:978-3-527-68913-2 MobiPocketISBN:978-3-527-68914-9 ePubISBN:978-3-527-68915-6 EditedbyChunyingChenandHaifangWang Biomedical Applications and Toxicology of Carbon Nanomaterials Editors AllbookspublishedbyWiley-VCHare carefullyproduced.Nevertheless,authors, Prof.Dr.ChunyingChen editors,andpublisherdonotwarrantthe NationalCtr.forNanoscience&Techn. informationcontainedinthesebooks, No.11,Beiyitiao includingthisbook,tobefreeoferrors. Zhongguancun Readersareadvisedtokeepinmindthat 100190Beijing statements,data,illustrations,procedural China detailsorotheritemsmayinadvertently beinaccurate. Prof.Dr.HaifangWang LibraryofCongressCardNo.:appliedfor ShanghaiUniversity Inst.ofNanochemistryandNanobiology 99ShangdaRd BritishLibraryCataloguing-in-Publication 200444Shanghai Data China Acataloguerecordforthisbookisavail- ablefromtheBritishLibrary. Cover gettyImages;Alamy Bibliographicinformationpublishedbythe DeutscheNationalbibliothek TheDeutscheNationalbibliothek liststhispublicationintheDeutsche Nationalbibliografie;detailed bibliographicdataareavailableonthe Internetat<http://dnb.d-nb.de>. ©2016Wiley-VCHVerlagGmbH&Co. KGaA,Boschstr.12,69469Weinheim, Germany Allrightsreserved(includingthoseof translationintootherlanguages).Nopart ofthisbookmaybereproducedinany form – byphotoprinting,microfilm,or anyothermeans – nortransmittedor translatedintoamachinelanguage withoutwrittenpermissionfromthe publishers.Registerednames,trademarks, etc.usedinthisbook,evenwhennot specificallymarkedassuch,arenottobe consideredunprotectedbylaw. PrintISBN:978-3-527-33871-9 ePDFISBN:978-3-527-69285-9 ePubISBN:978-3-527-69287-3 MobiISBN:978-3-527-69288-0 oBookISBN:978-3-527-69286-6 Typesetting SPiGlobal,Chennai,India Printedonacid-freepaper VII Contents ListofContributors XIX Preface XXV 1 Synthesis,Functionalization,andCharacterization 1 JianxunXu,XingLu,andBaowenLi 1.1 Introduction 1 1.2 FullerenesandMetallofullerenes 1 1.2.1 SynthesisandPurification 2 1.2.1.1 Synthesis 2 1.2.1.2 Purification 2 1.2.2 ChemicalFunctionalization 3 1.2.2.1 CarbeneReaction 3 1.2.2.2 Bingel–HirschReaction 4 1.2.2.3 PratoReaction 5 1.2.2.4 Bis-Silylation 5 1.2.2.5 Diels–AlderReactionandBenzyneReaction 5 1.2.2.6 SinglyBondedAddition 6 1.2.2.7 SupramolecularComplexesofEMFs 6 1.2.3 Characterization 6 1.2.3.1 SynchrotronRadiationPowderDiffraction (SRPD)/Rietveld/MEM 6 1.2.3.2 NuclearMagneticResonance(NMR)Spectroscopy 7 1.2.3.3 TheoreticalCalculation 7 1.2.3.4 Single-CrystalX-rayDiffractionCrystallography 7 1.2.3.5 Others 8 1.2.4 QuestionsandFutureDirections 8 1.3 CarbonNanotubes 8 1.3.1 Synthesis 9 1.3.1.1 ArcDischargeMethod 9 1.3.1.2 LaserAblationMethod 10 1.3.1.3 CVDMethod 10 1.3.1.4 SynthesisofCNTswithaDefinedStructure 10 1.3.2 Functionalization 11 VIII Contents 1.3.2.1 CovalentChemicalReactions 11 1.3.2.2 NoncovalentModifications 11 1.3.3 Characterization 12 1.3.3.1 MicroscopicCharacterizations 12 1.3.3.2 SpectroscopicCharacterizations 13 1.3.4 QuestionsandFutureDirections 13 1.4 Graphene 14 1.4.1 SynthesisandCharacterization 14 1.4.2 FunctionalizationofGrapheneandGrapheneOxide 17 1.4.3 ProspectsandChallenges 18 1.5 SummaryandOutlook 20 References 21 2 IdentificationandDetectionofCarbonNanomaterialsinBiological Systems 29 HaifangWang,Zheng-MeiSong,Yi-FanYang,AonengCao,andYuanfangLiu 2.1 Introduction 29 2.2 AvailableTechniquesforQualitativeandQuantitative Determination 30 2.2.1 OpticalMicroscopicObservation 30 2.2.2 ElectronMicroscopic(EM)Observation 31 2.2.3 RamanSpectroscopicMeasurement 33 2.2.4 FluorescenceAnalysis 36 2.2.4.1 IntrinsicFluorescenceAnalysis 36 2.2.4.2 LabeledFluorescenceAnalysis 39 2.2.5 IsotopeLabelingMethod 39 2.2.5.1 RadioisotopeLabeling 40 2.2.5.2 StableIsotopeLabeling 43 2.2.5.3 TipsforIsotopicLabeling 43 2.2.6 ChromatographicTechnique 45 2.2.7 FlowCytometryMethod 45 2.2.8 OtherMethods 46 2.3 SummaryandOutlook 47 Acknowledgments 48 References 48 3 BiodistributionandPharmacokineticsofCarbonNanomaterials InVivo 55 Sheng-TaoYang,XiaoyangLiu,andJingruXie 3.1 Introduction 55 3.2 AmorphousCarbonNanoparticles 55 3.2.1 UltrafineCarbonParticles 56 3.2.2 CarbonNanoparticles 58 3.2.3 CarbonDots 59 3.3 sp2CarbonNanomaterials 62