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Edited by @WILEY-YCH Paolo Samor' and Franco Cacialli Functional Supramolecular Arch itectu res For Organic Electronics and Nanotechnology Volume 1 Editedby PaoloSamor`ıand FrancoCacialli FunctionalSupramolecular Architectures RelatedTitles Siebbeles,L.D.A.,Grozema,F.C.(eds.) Atwood,J.L.,Steed,J.W.(eds.) ChargeandExcitonTransport OrganicNanostructures throughMolecularWires 2008 2011 ISBN:978-3-527-31836-0 ISBN:978-3-527-32501-6 Diederich,F.,Stang,P.J.,Tykwinski,R.R. Leclerc,M.,Morin,J.-F.(eds.) (eds.) DesignandSynthesisof ModernSupramolecular ConjugatedPolymers Chemistry StrategiesforMacrocycleSynthesis 2010 ISBN:978-3-527-32474-3 2008 ISBN:978-3-527-31826-1 Cosnier,S.,Karyakin,A.(eds.) Hadziioannou,G.,Malliaras,G.G.(eds.) Electropolymerization SemiconductingPolymers Concepts,MaterialsandApplications Chemistry,PhysicsandEngineering 2010 ISBN:978-3-527-32414-9 2007 ISBN:978-3-527-31271-9 Guldi,D.M.,Martín,N.(eds.) Samori,P.(ed.) CarbonNanotubesandRelated Structures ScanningProbeMicroscopies BeyondImaging Synthesis,Characterization,Functionali- zation,andApplications ManipulationofMoleculesand Nanostructures 2010 ISBN:978-3-527-32406-4 2006 ISBN:978-3-527-31269-6 Brabec,C.,Scherf,U.,Dyakonov,V.(eds.) OrganicPhotovoltaics Materials,DevicePhysics,and ManufacturingTechnologies 2008 ISBN:978-3-527-31675-5 Edited by Paolo Samorì and Franco Cacialli Functional Supramolecular Architectures for Organic Electronics and Nanotechnology Volume 1 TheEditors AllbookspublishedbyWiley-VCHarecarefully produced.Nevertheless,authors,editors,and Prof.Dr.PaoloSamorì publisherdonotwarranttheinformationcontained UniversitédeStrasbourgandCNRS(UMR7006) inthesebooks,includingthisbook,tobefreeof NanochemistryLaboratory,ISIS errors.Readersareadvisedtokeepinmindthat 8,alléeGaspardMonge statements,data,illustrations,proceduraldetailsor 67083StrasbourgCedex otheritemsmayinadvertentlybeinaccurate. France LibraryofCongressCardNo.: appliedfor Prof.Dr.FrancoCacialli DepartmentofPhysicsandAstronomy BritishLibraryCataloguing-in-PublicationData UniversityCollegeLondon Acataloguerecordforthisbookisavailablefromthe GowerStreet BritishLibrary. LondonWC1E6BT UnitedKingdom Bibliographicinformationpublishedby theDeutscheNationalbibliothek TheDeutscheNationalbibliothekliststhis publicationintheDeutscheNationalbibliografie; detailedbibliographicdataareavailableonthe Internetathttp://dnb.d-nb.de. #2011WILEY-VCHVerlag&Co.KGaA, Boschstr.12,69469Weinheim,Germany Allrightsreserved(includingthoseoftranslationinto otherlanguages).Nopartofthisbookmaybe reproducedinanyform–byphotoprinting, microfilm,oranyothermeans–nortransmittedor translatedintoamachinelanguagewithoutwritten permissionfromthepublishers.Registerednames, trademarks,etc.usedinthisbook,evenwhennot specificallymarkedassuch,arenottobeconsidered unprotectedbylaw. Composition ThomsonDigital,Noida,India PrintingandBinding betz-druckGmbH,Darmstadt CoverDesign Adam Design,Weinheim PrintedintheFederalRepublicofGermany Printedonacid-freepaper ISBN:978-3-527-32611-2 ToCristiana,EmmaandAnna and ToAnna,ChiaraandMarco VII Contents Preface XXIII ListofContributors XXV Volume1 PartOne ModelingandTheory 1 1 ChargeTransportinOrganicSemiconductors:AMultiscaleModeling 3 NicolasMartinelli,YoannOlivier,LucaMuccioli,AndreaMinoia, PatrickBrocorens,Mari-CarmenRuizDelgado,ClaudioZannoni, DavidBeljonne,RobertoLazzaroni,Jean-LucBrédas,andJérômeCornil 1.1 Introduction 3 1.2 OrganicSingleCrystals 6 1.2.1 MolecularParametersforChargeTransport 6 1.2.2 InfluenceofIntermolecularVibrations 9 1.2.3 ChargeMobilityValues 13 1.3 TetrathiafulvaleneDerivatives 15 1.4 PolythiopheneDerivatives 18 1.5 PhthalocyanineStacks 22 1.5.1 StructuralProperties 22 1.5.2 ChargeTransportProperties 25 1.6 PolymerDielectrics 27 1.6.1 ElectrostaticDisorder 29 1.6.2 ChargeMobilityValues 29 1.7 Outlook 31 References 33 2 MonteCarloStudiesofPhaseTransitionsandCooperativeMotion inLangmuirMonolayerswithInternalDipoles 39 ChristopherB.George,MarkA.Ratner,andIgalSzleifer 2.1 Introduction 39 2.2 ComputationalDetails 40 FunctionalSupramolecularArchitectures.EditedbyPaoloSamorìandFrancoCacialli Copyright(cid:2)2011WILEY-VCHVerlagGmbH&Co.KGaA,Weinheim ISBN:978-3-527-32611-2 VIII Contents 2.3 ResultsandDiscussion 42 2.3.1 UnchargedSystem 42 2.3.2 ChargedSystem 45 2.4 Summary 49 References 51 3 MoleculesonGoldSurfaces:WhatTheyDoandHowThey GoAroundtoDoIt 55 NadjaSändigandFrancescoZerbetto 3.1 Introduction 55 3.2 ASimpleDescriptionoftheGeometricalStructureofMetals 57 3.3 ASimpleDescriptionoftheGeometricalStructureofMolecules 58 3.4 ElectronegativityGovernsChemicalInteractions:ChargeEquilibration, QEq,Models 58 3.5 ASimpleDescriptionoftheInteractionbetweenMetalSurfaces andMolecules 59 3.6 PresenceofanExternalElectricPotentialorField 60 3.7 GeneralityoftheModelandItsTransferability 60 3.8 ThiolatesonGold 61 3.9 AdsorptionofaLargeMolecule:C 65 60 3.10 SimplePackingProblems 67 3.11 ThePresenceofanElectrostaticPotential 69 3.12 ChallengesandConclusion 71 References 72 PartTwo SupramolecularSyntheticChemistry 79 4 ConjugatedPolymerSensors:Design,Principles, andBiologicalApplications 81 MindyLevineandTimothyM.Swager 4.1 Introduction 81 4.1.1 Amplification 81 4.1.2 RoleofDimensionalityandSensoryMechanism 82 4.2 WaterSolubility 83 4.2.1 ConjugatedPolyelectrolytes 83 4.2.2 NonspecificBinding 84 4.2.3 NonionicWater-SolublePolymers 86 4.3 ProteinDetection 89 4.3.1 Introduction 89 4.3.2 ProteaseDetection 89 4.3.3 KinaseandPhosphataseDetection 93 4.3.4 LectinDetection 94 4.3.5 OtherProteinDetection 95 4.3.6 ProteinConformationDetection 96 4.4 DNADetection 97 Contents IX 4.4.1 Polythiophene-BasedDNADetection 97 4.4.2 FRET-BasedDNADetection 98 4.5 BacteriaDetection 101 4.5.1 Introduction 101 4.5.2 Mannose-ContainingPolymers 102 4.5.3 DetectionofBacterialExcretionProducts 103 4.6 Electron-DeficientPolymers 104 4.6.1 FluorinatedPPEs 104 4.7 Aggregation-BasedDetection 106 4.7.1 Introduction 106 4.7.2 DetectionviaPolymerQuenching 106 4.7.3 DetectionviaLow-EnergyEmission 108 4.8 Temperature-ResponsiveFluorescentPolymers 112 4.8.1 Introduction 112 4.8.2 Examples 112 4.9 NonhomogeneousDetectionSchemes 115 4.9.1 Introduction 115 4.9.2 CPsAdsorbedonSurfaces 116 4.9.3 CPParticlesfromCollapsedPolymerChains 119 4.10 MechanismofEnergyTransfer 122 4.10.1 Theory 122 4.10.2 ModificationstoFörsterTheory 123 4.10.3 EvidenceforDexter-TypeEnergyMigration 123 4.11 ConclusionsandFutureDirections 127 References 128 5 ChromophoricPolyisocyanideMaterials 135 BramKeereweer,ErikSchwartz,StéphaneLeGac,RoelandJ.M.Nolte, PaulH.J.Kouwer,andAlanE.Rowan 5.1 Introduction 135 5.2 PolyisocyanideMaterials 137 5.3 PerylenePolyisocyanidesinDevices 143 5.4 TFTDevices 147 5.5 MorphologyControlinPerylene/CrystalSystems 147 5.6 PostmodificationofPolyisocyanopeptides 149 5.7 TowardLargerLengthScales:PolyisocyanopeptideBrushes 151 5.8 SummaryandOutlook 152 References 152 6 FunctionalPolyphenylenesforSupramolecularOrdering andApplicationinOrganicElectronics 155 MartinBaumgartenandKlausMüllen 6.1 Introduction 155 6.2 ConjugatedPolymers 156 6.2.1 LinearandLadderizedPolyphenylenes 156

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