Organic Nanomaterials Synthesis, Characterization, and Device Applications PDF
Preview Organic Nanomaterials Synthesis, Characterization, and Device Applications
ORGANIC NANOMATERIALS ORGANIC NANOMATERIALS Synthesis, Characterization, and Device Applications Editedby TOMA´STORRES DepartamentodeQu´ımicaOrga´nica FacultaddeCiencias UniversidadAuto´nomadeMadrid Madrid,SpainandIMDEANanociencia C/Faraday9 CiudadUniversitariadeCantoBlanco Madrid,Spain GIOVANNIBOTTARI DepartamentodeQu´ımicaOrga´nica FacultaddeCiencias UniversidadAuto´nomadeMadrid Madrid,SpainandIMDEANanociencia C/Faraday9 CiudadUniversitariadeCantoBlanco Madrid,Spain Copyright(cid:2)C 2013byJohnWiley&Sons,Inc.Allrightsreserved. PublishedbyJohnWiley&Sons,Inc.,Hoboken,NewJersey. PublishedsimultaneouslyinCanada. 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QD262.O642013 620.1′17–dc23 2013000335 PrintedintheUnitedStatesofAmerica 10 9 8 7 6 5 4 3 2 1 CONTENTS Preface vii Contributors ix 1 AProposedTaxonomyandClassificationStrategyforWell-Defined, Soft-MatterNanoscaleBuildingBlocks 1 JørnB.ChristensenandDonaldA.Tomalia 2 OntheRoleofHydrogen-BondingintheNanoscaleOrganization ofπ-ConjugatedMaterials 33 AlbertusP.H.J.SchenningandDavidGonza´lez-Rodr´ıguez 3 ChiralOrganicNanomaterials 59 DavidB.Amabilino 4 BiochemicalNanomaterialsbasedonPoly(ε-caprolactone) 79 IrakliJavakhishviliandSørenHvilsted 5 Self-AssembledPorphyrinNanostructuresandtheir PotentialApplications 103 JohnA.ShelnuttandCraigJ.Medforth 6 NanostructuresandElectron-TransferFunctions ofNonplanarPorphyrins 131 ShunichiFukuzumiandTakahikoKojima 7 TweezersandMacrocyclesfortheMolecularRecognitionofFullerenes 147 DavidCanevet,EmilioM.Pe´rez,andNazarioMart´ın 8 Covalent,Donor–AcceptorEnsemblesbasedonPhthalocyanines andCarbonNanostructures 163 GiovanniBottari,MaxenceUrbani,andToma´sTorres 9 PhotoinducedElectronTransferofSupramolecularCarbonNanotube MaterialsDecoratedwithPhotoactiveSensitizers 187 FrancisD’Souza,AtulaS.D.Sandanayaka,andOsamuIto 10 InterfacingPorphyrins/PhthalocyanineswithCarbonNanotubes 205 JuergenBartelmeßandDirkM.Guldi v vi CONTENTS 11 OrganicSynthesisofEndohedralFullerenesEncapsulatingHelium, Dihydrogen,andWater 225 MichihisaMurata,YasujiroMurata,andKoichiKomatsu 12 FundamentalandAppliedAspectsofEndohedralMetallofullerenes asPromisingCarbonNanomaterials 241 MichioYamada,XingLu,LaiFeng,SatoruSato,YutaTakano, ShigeruNagase,andTakeshiAkasaka 13 AnUpdateonElectrochemicalCharacterizationandPotential ApplicationsofCarbonMaterials 259 Fang-FangLi,Adria´nVillalta-Cerdas,LourdesE.Echegoyen,andLuisEchegoyen 14 SolvatingInsolubleCarbonNanostructuresbyMolecularDynamics 311 MatteoCalvaresiandFrancescoZerbetto 15 InorganicCapsules:Redox-ActiveGuestsinMetalCages 331 AndrewMacdonellandLeroyCronin 16 Stimuli-ResponsiveMonolayers 347 FrancescaA.Scaramuzzo,MarioBarteri,PascalJonkheijm,andJurriaanHuskens 17 Self-AssembledMonolayersasModelBiosurfaces 369 AnnaLaromaineandCharlesR.Mace 18 Low-DimensionalityEffectsinOrganicFieldEffectTransistors 397 StefanoCasalini,TobiasCramer,FrancescaLeonardi,Massimiliano Cavallini,andFabioBiscarini 19 TheGrowthofOrganicNanomaterialsbyMolecularSelf-Assembly atSolidSurfaces 421 Jose´M.Gallego,RobertoOtero,andRodolfoMiranda 20 BiofunctionalizedSurfaces 447 MariselaVe´lez 21 CarbonNanotubeDerivativesasAnticancerDrugDeliverySystems 469 ChiaraFabbro,TatianaDaRos,andMaurizioPrato 22 PorousNanomaterialsforBiomedicalApplications 487 HenningLu¨lf,Andre´Devaux,EkoAdiPrasetyanto,andLuisaDeCola 23 DicationicGeminiNanoparticleDesignforGeneTherapy 509 MahmoudElsabahy,IldikoBadea,RonaldVerrall,McDonaldDonkuru, andMariannaFoldvari 24 SensingHg(II)IonsinWater:FromMoleculestoNanostructured MolecularMaterials 529 ImmaRatera,AlbertoTa´rraga,PedroMolina,andJaumeVeciana 25 OrganicNanomaterialsforEfficientBulkHeterojunctionSolarCells 549 PavelA.TroshinandNiyaziSerdarSariciftci 26 MesoscopicDye-SensitizedSolarCells 579 MohammadKhajaNazeeruddin,JaejungKo,andMichaelGra¨tzel Index 599 PREFACE Inthelastdecade,muchprogresshasbeenmadeinthefieldof by Javakhishvili and Hvilsted (Chapter 4), followed by organicnanomaterials.Recentdevelopmentsinnanoscience thoroughstudiesofself-assembledporphyrinnanostructures and nanotechnology have driven this field forward, thus and their potential applications by Shelnutt and Medforth allowing the preparation of novel materials with controlled (Chapter5);finally,electron-transferfunctionsofnonplanar morphology and well-defined properties, with clear and porphyrinsarestudiedbyFukuzumiandKojima(Chapter6). exciting technological applications. The new insights into Thesecondpartofthebookconsistsofaseriesofchap- theoptoelectronicpropertiesofmolecules,togetherwiththe tersdevotedtocarbonnanostructuresrangingfromfullerenes recent development of techniques such as scanning probe (including endohedral fullerenes) and carbon nanotubes to microscopy, among many others, have pushed chemists to graphene, which report on properties, theoretical studies, designnovelmolecularandsupramolecularfunctionalarchi- and applications. The supramolecular aspects of receptors tectures. The implications range from the basic molecular for the molecular recognition of fullerenes are described self-assembly of complementary organic systems, which by Canevet, Pe´rez, and Mart´ın (Chapter 7), whereas cova- constitute an important part of the so-called “bottom-up lent, donor–acceptor ensembles based on phthalocyanines approach” to exciting new applications of pure organic or andcarbonnanostructures,includinggraphene,arereviewed hybridmaterials,liketheonesexpectedforlowdimensional by Bottari, Urbani, and Torres (Chapter 8). Breakthroughs carbon nanostructures, such as fullerenes, nanotubes, and in the photophysics of carbon nanotubes are covered by graphenes, or the recent developments in molecular photo- twoexcellentcontributionsaddressing(a)thephotoinduced voltaics,forexample,innanostructuredhybridmaterialsfor electron-transfer properties of supramolecular carbon nan- energy conversion and storage. The aim of this book enti- otubematerialsdecoratedwithphotoactivesensitizers,out- tled Organic Nanomaterials: Synthesis, Characterization, lined by D’Souza, Sandanayaka, and Ito (Chapter 9), and and Device Applications, is to present an appropriate and (b) the study of the interactions of porphyrins and phthalo- representativecoverageofthesematerials,whichconstitute cyanines with carbon nanotubes, which is presented by oneofthemostactivelypursuedfieldsofscience. Bartelmeß and Guldi (Chapter 10). The next two chapters This book contains 26 chapters, which have been ratio- are dedicated to endohedral fullerenes, namely to the syn- nallyorganizedinfivemainparts.Thefirstpartisconcerned thesis of systems encapsulating helium, dihydrogen, and with introductory and general chapters on nanomaterials water, by Murata, Murata, and Komatsu (Chapter 11), and andself-assemblednanostructures.ChristensenandTomalia to fundamental and applied aspects of endohedral metallo- proposeaclassificationstrategyforwell-defined,soft-matter fullerenesbyAkasakaandco-workers(Chapter12).Inthese nanoscale building blocks (Chapter 1), Schenning and two interesting chapters, the authors present new insights Gonza´lez-Rodr´ıguez analyze the role of hydrogen bonding into the chemistry and properties of endohedral fullerenes. in the nanoscale organization of π-conjugated materials This block of the book mainly devoted to carbon nano- (Chapter 2), and Amabilino reviews some interesting structures is closed with an excellent update on electro- aspects of chiral, organic nanomaterials (Chapter 3). An chemical characterization and potential applications of car- overview of a class of biochemical nanomaterials is given bon materials by Echegoyen and co-workers (Chapter 13), vii viii PREFACE followedbyatheoreticalapproachtosolvatinginsolublecar- Thebookendswiththreecomprehensiveappliedchapters, bonnanostructuresbymoleculardynamicsbyCalvaresiand as examples of the potential use of organic nanostructured Zerbetto(Chapter14). materials in nanoscience, which are devoted to sensors and The third group of chapters focuses on different aspects molecular photovoltaics. This part starts with a chapter by of some inorganic materials, self-assembled monolayers, Ratera, Ta´rraga, Molina, and Vecianna which discusses the organicfieldeffecttransistors,andmolecularself-assembly sensingofHg(II)ionsinwater(Chapter24),anditisfollowed atsolidsurfaces.Thus,thetopicofinorganicmetalcapsules by two chapters on the main fields of organic solar cells, with redox-active guests is treated by Macdonell and namely,organicnanomaterialsforefficientbulkheterojunc- Cronin (Chapter 15), whereas the following two chapters tionsbyTroshinandSariciftci(Chapter25),andmesoscopic developed by Huskens and co-workers (Chapter 16) and dye-sensitized solar cells by Nazeeruddin, Ko, and Gra¨tzel by Laromaine and Mace (Chapter 17) review the use of (Chapter26). stimuli-responsive monolayers and self-assembled mono- Most chapters end with a summarizing conclusion that layers as model biosurfaces, respectively. Finally, the low- alsoservesasanabstract.Thecombinedauthorsofthechap- dimensionality effects in organic field effect are described tersgiveagoodrepresentationoftheorganicnanomaterials, by Biscarini and co-workers (Chapter 18), and the block is although with different styles as is often the case in multi- well-complementedbythegrowthoforganicnanomaterials authorbooks. by molecular self-assembly at solid surfaces, which is Finally, andmost importantly, weareindebted toallthe developedbyGallego,Otero,andMiranda(Chapter19). authorsforalltheireffortsinthepreparationoftheircontri- Thefourthpartofthebookconsistsofaseriesofchapters butions,whichwehopethereaderswillappreciate. dealing with different areas involving both biological Theeditorswouldliketodedicatethisbooktothemem- aspectsandnanomaterials.Inthispart,Ve´lezreportsonthe oryofourcolleagueandfriendChristianG.Claessens,who interesting area of biofunctionalized surfaces (Chapter 20), recentlypassedaway. whereasFabbro,DaRos,andPratodescribecarbonnanotube derivatives as anticancer drug delivery systems (Chapter Toma´sTorres 21), with a special attention to the medical applications of GiovanniBottari different kinds of carbon nanotube-based nanomaterials. Closing this section, a study on porous nanomaterials for biomedical applications is outlined by De Cola and UniversidadAuto´nomadeMadrid,Spain co-workers (Chapter 22), whereas Foldvari and co-workers April2013 reportonnanoparticledesignforgenetherapy(Chapter23).
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