Organic Nanomaterials Synthesis, Characterization, and Device Applications

627 Pages·2013·120.417 MB·English

by  Tomas Torres, Giovanni Bottari

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
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LibraryofCongressCataloging-in-PublicationData
Organicnanomaterials:synthesis,characterization,anddeviceapplications/[editedby]TomasTorres,GiovanniBottari.
pagescm
Includesindex.
ISBN978-1-118-01601-5(hardback)
1.Organiccompounds–Synthesis.2.Nanostructuredmaterials.I.Torres,Tomas,editorofcompilation.II.Bottari,Giovanni,editorofcompilation.
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).