Iridium (III) in Optoelectronic and Photonics Applications

731 Pages·2017·23.338 MB·English

by  Eli Zysman-Colman

Iridium(III)inOptoelectronicand
PhotonicsApplications
Iridium(III) in Optoelectronic and Photonics
Applications
Edited by
Eli Zysman-Colman
Organic Semiconductor Centre
EaStCHEM School of Chemistry
University of St Andrews
UK
Thiseditionfirstpublished2017
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LibraryofCongressCataloging-in-PublicationData
Names:Zysman-Colman,Eli,1975–editor.
Title:Iridium(III)inOptoelectronicandPhotonicsApplications/
editedbyEliZysman-Colman.
Description:Chichester,WestSussex:JohnWiley&Sons,Inc.,2017.|
Includesindex.
Identifiers:LCCN2016055403(print)|LCCN2016057073(ebook)|ISBN
9781119007135(cloth)|ISBN9781119007142(AdobePDF)|ISBN
9781119007159(ePub)
Subjects:LCSH:Iridium–Industrialapplications.|Iridiumalloys.|
Optoelectronicdevices.|Photonics.
Classification:LCCTP245.I7I742017(print)|LCCTP245.I7(ebook)|DDC
621.36/5–dc23
LCrecordavailableathttps://lccn.loc.gov/2016055403
CoverdesignbyWiley
Coverimage:(Background)©KlausFenzl/EyeEm/Gettyimages;
(TopImage)CourtesyofDanielAntónGarcía,UniversityofStAndrews,UK
Setin10/12ptWarnockbySPiGlobal,Pondicherry,India
10 9 8 7 6 5 4 3 2 1
Dedicated to myparents Margo and Neil whose support
has been continuous and unwavering
vii
Contents
ListofContributors xv
Foreword xvii
Preface xix
Volume1
1 ArchetypalIridium(III)CompoundsforOptoelectronicandPhotonic
Applications:PhotophysicalPropertiesandSyntheticMethods 1
JosephC.DeatonandFelixN.Castellano
1.1 Introduction 1
1.2 Iridium Complex Ion Dopants inSilver Halide Photographic Materials 1
1.3 Overview of the Photophysical Properties of C^N and C^C: Cyclometalated
Ir(III) Complexes 2
1.4 Importance of Ir─C Bonds inthe Archetypal Ir(III) Complexes for
Optoelectronic and Photonic Applications 9
1.5 Tuning Emission Color 14
1.6 Absorbance and Photoluminescence of C^N Cyclometalated Ir(III)
Complexes 17
1.7 SOC Mechanism: Radiative Decay Rates and ZFS 23
1.8 Non-RadiativeDecay Rates 39
1.9 Synthetic Methods Targeting C^N Cyclometalated Ir(III) Compounds 42
1.10 Synthetic Methods forCyclometalated Ir(III) Compounds Containing
Carbenes 47
1.11 Conclusions 48
Acknowledgements 49
Abbreviations forLigands in Ir(III) Complexes 49
References 50
2 MultinuclearIridiumComplexes 71
J.A.GarethWilliams
2.1 Introduction 71
2.2 Compounds Incorporating ‘Single Atom Bridges’: μ-Chloro, μ-Oxo
and μ-Aza 72
2.2.1 μ-Chloro-Bridged Complexes 72
2.2.2 μ-Aza-BridgedComplexes 74
2.2.3 μ-Hydroxo-BridgedComplexes 76
viii Contents
2.3 Polyatomic Acyclic Bridges: Acetylides, Cyanides and Hydrazides 78
2.4 Compounds with Heterocyclic Bridges 82
2.4.1 Bis-(N^N)-CoordinatingLigandsandRelatedSystemsIncorporatingAtLeast
One N^N Unit 83
2.4.2 Bis-(N^C)-Coordinating Ligands 89
2.5 Multinuclear Complexes Featuring Conjugated Bridges between Iridium-
Bound Polypyridyl or ArylpyridylLigands 93
2.5.1 Systems Incorporating C≡C or N=N Bridges withOne or More
[Ir(N^C) (N^N)]+ Units 95
2
2.5.2 Multinuclear Complexes Incorporating Phenyl and Polyphenylene Bridges
between the Ligands: ‘Supramolecular Assemblies’ 96
2.6 Concluding Remarks 104
Acknowledgements 104
References 104
3 SoftMaterialsandSoftSaltsBasedonIridiumComplexes 111
EtienneBaranoffandYafeiWang
3.1 Introduction 111
3.2 Liquid Crystals 112
3.3 Gels 115
3.4 Micelles 116
3.5 Langmuir–Blodgett Films 118
3.6 Soft Salts 118
3.7 Conclusion 123
Acknowledgements 123
References 123
4 PorousMaterialsBasedonPreciousMetalBuildingBlocksforSolarEnergy
Applications 127
DanielMicheroniandWenbinLin
4.1 Introduction 127
4.2 The Luminescent Nature of MOFs and Their Use inChemical
Applications 129
4.3 Energy Transfer in Porous Materials 134
4.4 Porous Materials for Water Oxidation 136
4.5 Porous Materials for Proton Reduction 138
4.6 Porous Materials for CO Reduction 140
2
4.7 Conclusionsand Outlook 141
References 141
5 PolymericArchitecturesContainingPhosphorescentIridium(III)
Complexes 145
AndreasWinterandUlrichS.Schubert
5.1 Introduction 145
5.2 Ir(III)-Containing Polymers: Classification,Design Principles, and
Syntheses 146
5.2.1 Classification of Ir(III)-Containing Polymers 146
5.2.2 Design Principles for Metal-Containing Polymers 147
Contents ix
5.2.2.1 Decoration of Preformed Polymers with Ir(III) Complexes 149
5.2.2.2 Coordination of Ir(III) Precursor Complexes
to Preformed Polymers 151
5.2.2.3 (Co)Polymerization of Ir(III)-Containing Monomers 157
5.2.2.4 Electropolymerization of Ir(III)-ContainingComplexes 182
5.2.2.5 Synthetic Approaches Toward Ir(III)-ContainingPolymers: The Roads Not
Taken 186
5.3 Hyperbranched and Dendritic Architectures 187
5.3.1 Ir(III)-Containing Hyperbranched Polymers 187
5.3.2 Ir(III)-Containing Dendritic Systems 188
5.4 Concluding Remarks 191
References 192
6 Iridium(III)ComplexesforOLEDApplication 205
ElenaLonghiandLuisaDeCola
6.1 Introduction 205
6.2 Iridium Complexes 206
6.2.1 General Synthesis of Ir(III) Complexes 207
6.2.2 Luminescence of Iridium(III) Complexes 208
6.2.3 Emission Color Tuningin Iridium(III) Complexes 209
6.2.3.1 Influence of the (C^N) Ligand 210
6.2.3.2 Influence of the Ancillary Ligand 212
6.3 Organic Light-Emitting Diodes 216
6.3.1 Device Architecture and Fabrication 217
6.3.2 Device Lifetime 218
6.3.3 Device Efficiency 220
6.3.4 Phosphorescent Materials 221
6.3.5 Host Materials 222
6.4 Iridium(III) Complexes for PHOLED Application 227
6.4.1 Green Emitters 227
6.4.1.1 Role of the Ancillary Ligand 228
6.4.1.2 Modification of the Phenylpyridine Ring 229
6.4.1.3 Use of Different Tris-cyclometalatedMotifs 230
6.4.2 Red Emitters 232
6.4.3 Blue Emitters 238
6.5 Conclusionsand Perspectives 262
References 262
7 AComprehensiveReviewofLuminescentIridiumComplexesUsedin
Light-EmittingElectrochemicalCells(LEECs) 275
AdamF.HenwoodandEliZysman-Colman
7.1 Introduction 275
7.2 Device Fundamentals 278
7.3 Green Emitters 280
7.3.1 Archetypal Emitters 282
7.3.2 Pyrazoles 289
7.3.3 Imidazoles 292
7.3.4 Triazoles and Tetrazoles 293
x Contents
7.3.5 Oxadiazoles 294
7.3.6 Thiophenes 296
7.3.7 Intramolecular π-Stacked Emitters 296
7.3.8 Supramolecular Emitters 300
7.4 Blue Emitters 301
7.4.1 [Ir(ppy) (bpy)]+-TypeEmitters 302
2
7.4.2 Pyrazoles 307
7.4.3 Imidazoles 312
7.4.4 Triazoles 313
7.4.5 Oxadiazoles 316
7.4.6 N-Heterocyclic Carbenes 320
7.4.7 Phosphines 322
7.5 Yellow Emitters 323
7.5.1 [Ir(ppy) (bpy)]+-TypeEmitters 324
2
7.5.2 Imidazole Emitters 327
7.5.3 Anionic Emitters 328
7.5.4 Intramolecularly π-Stacked Emitters 328
7.5.5 Multifunctional or Supramolecular Emitters 332
7.6 Orange-Red Emitters 334
7.6.1 [Ir(ppy) (bpy)]+-TypeEmitters 335
2
7.6.2 Emitters Bearing Five-MemberedHeterocyclic Rings 340
7.6.3 Intramolecular π-Stacked Emitters 341
7.6.4 Multifunctional Emitters 345
7.7 Conclusionsand Outlook 348
Acknowledgements 349
References 349
Volume2
8 ElectrochemiluminescenceofIridiumComplexes 359
SarahE.LairdandConorF.Hogan
8.1 Background and Overview of Electrochemiluminescence 359
8.1.1 ECL from Metal Complexes 362
8.2 Iridium ECL 363
8.2.1 First Examples 363
8.2.2 RenewedInterest in Iridium ECL Stimulated by Progress in the Field of
Light-Emitting Devices 364
8.2.3 Early Advances inTheoretical Understanding and Electrochemiluminophore
Design 366
8.2.4 Modified Electrode Systems 370
8.2.5 ECL-Based Sensing Strategies 372
8.2.6 IssuesRelatedtoECLofIridiumComplexesinAqueousMediaandQuenching
by Oxygen 384
8.2.7 TuningECL EmissionColour and RedoxProperties 386
8.2.8 Potential-Resolved Multicolour ECL 399
8.2.8.1 Miscellaneous ECL Systems Involving Iridium Complexes 405
8.2.9 Conclusionand Future Prospects 406
List of Ligand Abbreviations Used in Text 406
References 407
Contents xi
9 StrategicApplicationsofLuminescentIridium(III)Complexesas
BiomolecularProbes,CellularImagingReagents,andPhotodynamic
Therapeutics 415
KarsonKa-ShunTsoandKennethKam-WingLo
9.1 Introduction 415
9.2 General Cellular Staining Reagents 416
9.3 Hypoxia SensingProbes 423
9.4 Molecular and Ion Intracellular Probes 427
9.4.1 Intracellular Probes for Sulfur-Containing Species 427
9.4.2 Intracellular Probes for Metal Ions 433
9.4.3 Intracellular Probes for Hypochlorous Acid and Hypochlorite 437
9.4.4 Intracellular Probes for Nitric Oxide 439
9.5 Organelle-Targeting Bioimaging Reagents 441
9.5.1 Nucleus 441
9.5.2 Nucleoli 443
9.5.3 Golgi Apparatus 445
9.5.4 Mitochondria 447
9.6 Functionalized Polypeptides for Bioimaging 450
9.7 Polymers and Nanoparticles forBioimaging 454
9.8 Photocytotoxic Reagents and Photodynamic Therapeutics 458
9.9 Conclusion 466
Acknowledgements 466
Abbreviations 466
References 469
10 IridiumComplexesintheDevelopmentofOpticalSensors 479
TeresaRamón-Márquez,MartaMarín-Suárez,AlbertoFernández-Gutiérrez
andJ.F.Fernández-Sánchez
10.1 Generalitiesof Optical Sensors 479
10.2 Ir(III) Used as Optical Probes 481
10.2.1 Optical Probes for the Detection of Gaseous Species 481
10.2.1.1 Oxygen 482
10.2.1.2 Other Gaseous Species 483
10.2.2 Optical Probes for the Detection of Ionic Species 485
10.2.2.1 Cations 485
10.2.2.2 pH 491
10.2.2.3 Anions 493
10.2.3 Optical Probes for the Detection of Biomolecules 498
10.2.3.1 Amino Acids and Proteins 498
10.2.3.2 Nucleotides and Nucleic Acids 506
10.2.4 Optical Probes for the Detection of Other Small Molecules 506
10.2.4.1 Explosives 506
10.2.4.2 Free Radicals 507
10.2.4.3 H O 508
2 2
10.2.4.4 Amines 508
10.2.4.5 Silver Salts 508
10.2.4.6 HypochlorousAcid (HOCl) 508
10.3 Ir(III) Used in the Development of Sensing Phases 509
10.3.1 Sensing Phases forthe Detection of Gases 509
xii Contents
10.3.1.1 Oxygen 509
10.3.1.2 Others Gases 516
10.3.2 Sensing Phases for the Detection of Ions 516
10.3.3 Sensing Phases for the Detection of Biomolecules 517
10.3.3.1 Glucose 518
10.3.3.2 BSA 520
10.3.3.3 Cysteine and Homocysteine 520
10.3.3.4 Heparin 520
10.3.3.5 Histone 521
10.3.4 Sensing Phases for Multiparametric Sensing 521
10.4 Conclusionand Future Challenges 522
Acronyms Used inthe Names of the Complexes 525
References 528
11 PhotoredoxCatalysisofIridium(III)-BasedPhotosensitizers 541
TimothyM.MonosandCoreyR.J.Stephenson
11.1 Introduction 541
11.1.1 Photoredox Catalysis 541
11.1.2 Principles of Photoredox Catalysis 542
11.1.3 Iridium(III)Photocatalyst Design 542
11.1.4 Ir(III) Photocatalyst synthesis 545
11.2 Iridium-Based Photoredox Catalysis inOrganic Synthesis 547
11.2.1 Net Oxidative Reactions 547
11.2.1.1 Amine Oxidation and Functionalization 547
11.2.1.2 Arene Oxidation 551
11.2.2 Net Reductive Reactions 551
11.2.2.1 Dehalogenation Reactions 551
11.2.2.2 Ketyl Radical Chemistry 553
11.2.3 Redox-Neutral Reactions 554
11.2.3.1 Atom Transfer Radical Addition 555
11.2.3.2 Radical-Based Arene Addition Reactions 561
11.2.3.3 TandemCatalysis Methods 565
11.2.4 Amine Fragmentation 571
11.3 Conclusion 574
References 574
12 SolarFuelGeneration:StructuralandFunctionalEvolutionofIridium
Photosensitizers 583
HusainN.Kagalwala,DanielleN.ChirdonandStefanBernhard
12.1 Introduction 583
12.2 Fundamentals of [Ir(C^N) (N^N)]+Photosensitizers 585
2
12.2.1 Synthesis and Structure 585
12.2.2 Electronics:Photophysicsand Electrochemistry 585
12.2.3 Complexes Made to Order 588
12.3 Application of [Ir(C^N) (N^N)]+inPhotocatalytic Water Reduction 589
2
12.3.1 Initial Exploration 589
12.3.2 Systems with Non-precious Components 591
12.3.3 Strategies for Improved Efficiency 594