Photochromic Materials: Preparation, Properties and Applications

430 Pages·2016·17.34 MB·English

by  He Tian, Junji Zhang

Editedby
HeTianandJunjiZhang
PhotochromicMaterials
EditedbyHeTianandJunjiZhang
Photochromic Materials
Preparation,PropertiesandApplications
Editors AllbookspublishedbyWiley-VCH
arecarefullyproduced.Nevertheless,
Dr.HeTian authors,editors,andpublisherdonot
EastChinaUniversityofScience warranttheinformationcontainedin
andTechnology thesebooks,includingthisbook,to
KeyLaboratoryforAdvancedMaterials befreeoferrors.Readersareadvised
200237Shanghai tokeepinmindthatstatements,data,
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Dr.JunjiZhang
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V
Contents
ListofContributors XI
1 Introduction:OrganicPhotochromicMolecules 1
KeitaroNakatani,JonathanPiard,PeiYu,andRémiMétivier
1.1 PhotochromicSystems 1
1.1.1 GeneralIntroduction 1
1.1.2 BasicPrinciples 4
1.1.3 PhotochromicMolecules:SomeHistory 5
1.2 OrganicPhotochromicMolecules:MainFamilies 8
1.2.1 ProtonTransfer 9
1.2.2 Trans–CisPhotoisomerization 12
1.2.3 HomolyticCleavage 13
1.2.4 CyclizationReaction 14
1.2.4.1 Spiropyrans,Spirooxazines,andChromenes 14
1.2.4.2 FulgidesandFulgimides 17
1.2.4.3 Diarylethenes 18
1.3 MolecularDesigntoImprovethePerformance 20
1.3.1 FiguresofMerit 20
1.3.2 FatigueResistance:IncreasingtheNumberofOperatingCycles 21
1.3.3 Bistability:AvoidingUnwantedThermalBack-Reactioninthe
Dark 23
1.3.3.1 InfluenceofEthenicBridgeontheThermalStabilityoftheB
Form 24
1.3.3.2 ImpactoftheHeteroarylSubstituentsontheThermalStabilityofthe
BForm 24
1.3.4 FastPhotochromicSystems:RevertingBackSpontaneouslytothe
ColorlessStateinaGlance 25
1.3.5 GainingEfficiencyofthePhotoreaction:theExampleof
Diarylethenes 26
1.4 Conclusion 31
IrradiationataSpecificWavelength:IsosbesticPoint 32
VI Contents
CaseA:WhentheThermalBack-ReactionisNegligibleComparedto
thePhotochemicalReaction(TypicallyP-type) 33
CaseB:WhentheThermalBack-ReactionisMoreEfficientthanthe
PhotochemicalB→AReaction(TypicallyType) 34
References 34
2 PhotochromicTransitionalMetalComplexesfor
Photosensitization 47
Chi-ChiuKoandVivianWing-WahYam
2.1 Introduction 47
2.2 PhotosensitizationofStilbene-andAzo-ContainingLigands 48
2.3 PhotosensitizationofSpirooxazine-ContainingLigands 51
2.4 PhotosensitizationofDiarylethene-ContainingLigands 54
2.5 PhotosensitizationofPhotochromicN∧C-Chelate
Organoboranes 63
2.6 Conclusion 65
References 66
3 Multi-addressablePhotochromicMaterials 71
ShangjunChen,WenlongLi,andWeihongZhu
3.1 MolecularLogicGates 71
3.1.1 Two-InputLogicGates 71
3.1.2 CombinatorialLogicSystems 74
3.1.2.1 Half-AdderandHalf-Subtractor 74
3.1.2.2 KeypadLocks 77
3.1.2.3 DigitalEncoderandDecoder 82
3.2 DataStorageandMolecularMemory 84
3.2.1 FluorescenceSpectroscopy 85
3.2.2 InfraredSpectroscopy 90
3.2.3 OpticalRotation 92
3.3 GatedPhotochromores 95
3.3.1 HydrogenBonding 95
3.3.2 Coordination 98
3.3.3 ChemicalReaction 99
References 105
4 PhotoswitchableSupramolecularSystems 109
GuangleiLv,LiangChen,HaichuangLan,andTaoYi
4.1 Introduction 109
4.2 PhotoreversibleAmphiphilicSystems 110
4.2.1 PhotoreversibleDiarylethene-BasedAmphiphilicSystem 110
4.2.2 PhotoreversibleAzobenzene-BasedAmphiphilicSystem 116
4.2.3 PhotoreversibleSpiropyran-BasedAmphiphilicSystem 119
4.3 PhotoswitchableHost–GuestSystems 122
4.3.1 PhotocontrolledSupramolecularSelf-Assembly 123
Contents VII
4.3.2 PhotocontrolledCaptureandReleaseofGuestMolecules 128
4.3.3 FluorescentSwitchingPromotedbyHost–GuestInteraction 133
4.3.4 PhotoswitchableMolecularDevices 137
4.4 PhotochromicMetalComplexesandSensors 141
4.4.1 MetalComplexeswithAzobenzeneGroups 141
4.4.2 MetalComplexeswithDiaryletheneGroups 144
4.4.3 MetalComplexeswithSpirocyclicGroups 150
4.4.4 MetalComplexeswithRhodamine 152
4.5 OtherLight-ModulatedSupramolecularInteractions 153
4.6 ConclusionsandOutlook 159
References 159
5 Light-GatedChemicalReactionsandCatalyticProcesses 167
RobertGöstl,AnttiSenf,andStefanHecht
5.1 Introduction 167
5.2 GeneralDesignConsiderations 169
5.3 PhotoswitchableStoichiometricProcesses 171
5.3.1 StartingMaterialControl 172
5.3.2 ProductControl 175
5.3.3 StartingMaterialandProductControl 177
5.3.4 TemplateControl 178
5.4 PhotoswitchableCatalyticProcesses 182
5.4.1 ActivityControl 182
5.4.2 SelectivityControl 185
5.5 Outlook 187
References 190
6 SurfaceandInterfacialPhotoswitches 195
JunjiZhangandHeTian
6.1 PhotochromicSAMs 196
6.1.1 PhotochromicElectrodeSAMs 196
6.1.2 PhotoreversibleFunctionalSurfaces 198
6.1.2.1 PhotoswitchableSurfaceWettability 198
6.1.2.2 PhotocontrolledCapture-and-ReleaseSystem 202
6.1.2.3 SmartPhotochromicSurfaceBasedonSupramolecular
Systems 203
6.1.2.4 PhotochromicSurfaceforMolecularDataProcessing 205
6.2 PhotoregulatedNanoparticles 206
6.2.1 PhotochromicSwitchesonTraditionalMetalNanoparticles 208
6.2.1.1 PhotoswitchingontheMetalNanoparticles 208
6.2.1.2 PhotoinducedReversibleAggregationofNanoparticlesandTheir
VersatileApplications 210
6.2.2 PhotochromicSwitchesonOtherNovelFunctional
Nanoparticles 215
6.2.2.1 PhotoswitchableMagneticNanoparticles 215
VIII Contents
6.2.2.2 PhotomanipulatedQuantumDots 215
6.2.2.3 PhotochromicwithUpconversionNanoparticles 218
6.2.3 PhotocontrolledMesoporousSilicaNanoparticles 220
6.2.3.1 Photo-nanovalves 220
6.2.3.2 Photo-nanoimpellers 223
6.2.3.3 NIRLight-TriggeredMSNDrugDeliveryandTherapeutic
Systems 224
6.3 PhotocontrolledSurfaceConductance 226
6.3.1 PhotochromicConductanceSwitchingBasedonSAMs 226
6.3.2 PhotochromicConductanceonSingle-MoleculeLevel 228
References 231
7 HybridOrganic/PhotochromicApproachestoGenerate
MultifunctionalMaterials,Interfaces,andDevices 243
EmanueleOrgiuandPaoloSamorì
7.1 Introduction 243
7.1.1 TuningtheChargeInjectioninOrganic-BasedDevicesbyMeansof
PhotochromicMolecules 245
7.2 TuningthePolaronicTransportinOrganicSemiconductorsby
MeansofPhotochromicMolecules 251
7.2.1 PhotochromicMoleculesandOrganicSemiconductorsIncorporated
inDyads,Multiads,andPolymers 251
7.2.2 TheMultilayerApproach 254
7.2.3 TheBlendingApproach 255
7.3 PhotoresponsiveDielectricInterfacesandBulk 262
7.4 ConclusionsandFutureOutlooks 267
Acknowledgments 268
References 268
8 PhotochromicBulkMaterials 281
MasakazuMorimoto,SeiyaKobatake,MasahiroIrie,HariKrishnaBisoyi,
QuanLi,ShengWang,andHeTian
8.1 PhotochromicPolymers 281
8.1.1 GlassTransitionTemperature 281
8.1.2 Fluorescence 283
8.1.3 Conductivity 287
8.1.4 LivingRadicalPolymerization 288
8.1.5 SurfaceReliefGrating 290
8.1.6 PhotomechanicalEffect 290
8.2 Single-CrystallinePhotoswitches 293
8.2.1 Crystalline-StatePhotochromicMaterials 293
8.2.2 PhotochromicDiaryletheneSingleCrystals 293
8.2.3 InsituX-rayCrystallographicAnalysisofPhotoisomerization
Reaction 295
8.2.4 PhotoisomerizationQuantumYields 296
Contents IX
8.2.5 MulticolorPhotochromismofMulticomponentCrystals 297
8.2.6 NanoperiodicStructuresFabricatedbyPhotochromic
Reactions 299
8.2.7 PhotoinducedShapeChangesandMechanicalPerformance 301
8.3 PhotochromicLiquidCrystals 305
8.3.1 Introduction 305
8.3.2 Spiropyran-andSpirooxazine-BasedPhotochromicLiquid
Crystals 309
8.3.3 Diarylethene-BasedPhotochromicLiquidCrystals 314
8.3.4 Azobenzene-BasedPhotochromicLiquidCrystals 320
8.3.5 OtherPhotochromicLiquidCrystals 327
8.3.6 ConclusionsandOutlook 328
8.4 PhotochromicGels 329
8.4.1 Introduction 329
8.4.2 AzobenzeneGels 330
8.4.3 SpiropyranandSpirooxazineGels 335
8.4.4 DiarylethenesGels 337
8.4.5 NaphthopyranGels 342
8.4.6 TheOtherPhotochromicGels 343
8.4.7 Conclusion 346
References 346
9 PhotochromicMaterialsinBiochemistry 361
DanielleWilsonandNeilR.Branda
9.1 Introduction 361
9.2 ReversiblePhotochemicalSwitchingofBiomaterialFunction 362
9.3 GeneralDesignStrategiesandConsiderations 362
9.3.1 PhotoswitchableTethers 364
9.3.1.1 TheIncorporationMethod 364
9.3.1.2 Considerations 364
9.3.2 PhotoswitchableSmallMolecules 365
9.3.2.1 TheIncorporationMethod 365
9.3.2.2 Considerations 365
9.3.3 ChromophoreSelection 367
9.4 SelectedExamples 367
9.4.1 PhotoswitchableEnzymes 367
9.4.1.1 Drug-InspiredSmallMoleculeInhibitors 367
9.4.1.2 PhosphoribosylIsomeraseInhibitorwithTwoBindingUnits 370
9.4.1.3 DirectModificationofEnzymeswithPhotochromicGroups 372
9.4.2 PhotoswitchablePeptidesandProteins 373
9.4.2.1 PeptideCross-Linking 373
9.4.2.2 CyclicAntimicrobialPeptide 375
9.4.2.3 GeneticallyEncodedAminoAcids 376
9.4.2.4 ControlofMotorProteinFunctionUsingSite-Selective
Mutation 377
X Contents
9.4.3 PhotoswitchableIonChannelsandReceptors 379
9.4.3.1 PhotocontrolofChannelActivationandDesensitizationwitha
TetheredGlutamate 380
9.4.3.2 PhotocontrolofInsulinReleaseUsingaSmallMolecular
Sulfonylurea 380
9.4.3.3 PhotocontrolofReceptorsUsingRedLight 381
9.4.4 PhotoswitchableNucleotides 382
9.4.4.1 Spiropyran-ModifiedOligonucleotideBackbones 382
9.4.4.2 ControllingRNADuplexHybridizationwithLight 384
9.4.4.3 Diarylethene-ModifiedOligonucleotides 385
9.5 Summary 386
References 386
10 IndustrialApplicationsandPerspectives 393
JunjiZhangandHeTian
10.1 IndustrializationandCommercializationofOrganicPhotochromic
Materials 393
10.1.1 CommercializedT-typePhotochromicMaterials 395
10.1.2 CommercializedP-TypePhotochromicMaterials 398
10.2 PerspectivesforOrganicPhotochromicMaterials 399
References 409
Index 417
XI
ListofContributors
HariKrishnaBisoyi ShangjunChen
KentStateUniversity ShanghaiNormalUniversity
LiquidCrystalInstituteand KeyLaboratoryofResource
ChemicalPhysics ChemistryofMinistryof
InterdisciplinaryProgram Education
Kent ShanghaiKeyLaboratoryofRare
OH44242 EarthFunctionalMaterials
USA DepartmentofChemistry
200234Shanghai
NeilR.Branda China
SimonFraserUniversity
4DLABS,Departmentof RobertGöstl
Chemistry Humboldt-UniversitätzuBerlin
8888UniversityDrive DepartmentofChemistry
Burnaby Brook-Taylor-Str.2
BCV5A1S6 12489Berlin
Canada Germany
LiangChen StefanHecht
FudanUniversity Humboldt-UniversitätzuBerlin
DepartmentofChemistryand DepartmentofChemistry
ConcertedInnovationCenterof Brook-Taylor-Str.2
ChemistryforEnergyMaterials 12489Berlin
220HandanRoad Germany
200433Shanghai
China