Aggregation-Induced Emission

ANJUN QIN, Department of Polymer Science and Engineering, Zhejiang University, China. BEN ZHONG TANG, Department of Chemistry, The Hong Kong University of Science and Technology, China.

List of Contributors xi Preface xiii

1 AIE or AIEE Materials for Electroluminescence Applications 1

Chiao-Wen Lin and Chin-Ti Chen

1.1 Introduction 1

1.2 EL Background, EL Efficiency, Color Chromaticity, and Fabrication Issues of OLEDs 2

1.3 AIE or AIEE Silole Derivatives for OLEDs 7

1.4 AIE or AIEE Maleimide and Pyrrole Derivatives for OLEDs 10

1.5 AIE or AIEE Cyano-Substituted Stilbenoid and Distyrylbenzene Derivatives for OLEDs 14

1.6 AIE or AIEE Triarylamine Derivatives for OLEDs 17

1.7 AIE or AIEE Triphenylethene and Tetraphenylethene Derivatives for OLEDs 17

1.8 White OLEDs Containing AIE or AIEE Materials 31

1.9 Perspectives 36

References 37

2 Crystallization-Induced Phosphorescence for Purely Organic Phosphors at Room Temperature and Liquid Crystals with Aggregation-Induced Emission Characteristics 42

Wang Zhang Yuan, Yongming Zhang, and Ben Zhong Tang

2.1 Crystallization-Induced Phosphorescence for Purely Organic Phosphors at Room Temperature 42

2.1.1 Introduction 42

2.1.2 Molecular luminogens with crystallization-induced phosphorescence at room temperature 43

2.2 Liquid crystals with aggregation-induced emission characteristics 51

2.2.1 Luminescent liquid crystals 51

2.2.2 Aggregation-induced emission strategy towards high-efficiency luminescent liquid crystals 52

2.3 Conclusions and Perspectives 56

References 57

3 Mechanochromic Aggregation-Induced Emission Materials 60

Zhenguo Chi and Jiarui Xu

3.1 Introduction 60

3.2 Mechanochromic Non-AIE Compounds 61

3.3 Mechanochromic AIE Compounds 63

3.4 Conclusion 81

References 82

4 Chiral Recognition and Enantiomeric Excess Determination Based on Aggregation-Induced Emission 86

Yan-Song Zheng

4.1 Introduction to Chiral Recognition 86

4.2 Chiral Recognition and Enantiomeric Excess Determination of Chiral Amines 87

4.3 Chiral Recognition and Enantiomeric Excess Determination of Chiral Acids 90

4.3.1 Enantiomeric excess determination of chiral acids using chiral AIE amines 90

4.3.2 Enantiomeric excess determination of chiral acids using a chiral receptor in the presence of an AIE compound 97

4.4 Mechanism of chiral recognition based on AIE 100

4.4.1 Mechanism of chiral recognition by a chiral AIE monoamine 101

4.4.2 Mechanism of chiral recognition by a chiral AIE diamine 101

4.5 Prospects for chiral recognition based on AIE 103

References 104

5 AIE Materials Towards Efficient Circularly Polarized Luminescence, Organic Lasing, and Superamplified Detection of Explosives 106

Jianzhao Liu, Jacky W.Y. Lam, and Ben Zhong Tang

5.1 Introduction 106

5.2 AIE Materials with Efficient Circularly Polarized Luminescence and Large Dissymmetry Factor 106

5.2.1 Aggregation-induced circular dichroism 107

5.2.2 AIE, fluorescence decay dynamics and theoretical understanding 109

5.2.3 Aggregation-induced circularly polarized luminescence 112

5.2.4 Supramolecular assembly and structural modeling 114

5.3 AIE Materials for Organic Lasing 117

5.3.1 Fabrication of nano-structures 117

5.3.2 Lasing performances 118

5.4 AIE Materials for Superamplified Detection of Explosives 120

5.4.1 Hyperbranched polymer-based sensor 121

5.4.2 Mesoporous material-based sensor 126

5.5 Conclusion 126

References 127

6 Aggregation-Induced Emission and Applications of Aryl-Substituted Pyrrole Derivatives 129

Bin Tong and Yuping Dong

6.1 Introduction 129

6.2 Luminescence Properties of Triphenylpyrrole Derivatives in the Aggregated State 130

6.3 Applications 134

6.4 Aggregation-Induced Emission of Pentaphenylpyrrole 145

6.5 AIEE Mechanism of Pentaphenylpyrrole 148

6.6 Conclusion 150

References 150

7 Biogenic Amine Sensing with Aggregation-Induced Emission-Active Tetraphenylethenes 154

Takanobu Sanji and Masato Tanaka

7.1 Introduction 154

7.1.1 Biogenic amines 154

7.1.2 Sensing methods for biogenic amines 154

7.2 Fluorimetric Sensing of Biogenic Amines with AIE-Active TPEs 155

7.2.1 Design for fluorimetric sensing of biogenic amines 155

7.2.2 Sensing studies and statistical analysis 155

7.2.3 Determination of histamine concentration 159

7.2.4 Fluorimetric sensing of melamine with AIE-active TPEs 160

7.3 Summary and Outlook 160

References 161

8 New Chemo-/Biosensors with Silole and Tetraphenylethene Molecules Based on the Aggregation and Deaggregation Mechanism 162

Ming Wang, Guanxin Zhang, and Deqing Zhang

8.1 Introduction 162

8.2 Cation and Anion Sensors 163

8.3 Fluorimetric Biosensors for Biomacromolecules 166

8.4 Fluorimetric Assays for Enzymes 170

8.5 Fluorimetric Detection of Physiologically Important Small Molecules 177

8.6 Miscellaneous Sensors 180

8.7 Conclusion and Outlook 182

References 182

9 Carbohydrate-Functionalized AIE-Active Molecules as Luminescent Probes for Biosensing 186

Qi Chen and Bao-Hang Han

9.1 Introduction 186

9.2 Carbohydrate-Bearing AIE-Active Molecules 187

9.2.1 Carbohydrate-bearing siloles 188

9.2.2 Carbohydrate-bearing phosphole oxides 189

9.2.3 Carbohydrate-bearing tetraphenylethenes 190

9.3 Luminescent Probes for Lectins 192

9.4 Luminescent Probes for Enzymes 196

9.5 Luminescent Probes for Viruses and Toxins 200

9.6 Conclusion 202

Acknowledgments 202

References 202

10 Aggregation-Induced Emission Dyes for In Vivo Functional Bioimaging 205

Jun Qian, Dan Wang, and Sailing He

10.1 Introduction 205

10.2 AIE Dyes for Macro In Vivo Functional Bioimaging 206

10.2.1 AIE dye-encapsulated phospholipid–PEG nanomicelles 206

10.2.2 AIE dye-encapsulated nanomicelles for SLN mapping of mice 206

10.2.3 AIE dye-encapsulated nanomicelles for tumor targeting of mice 212

10.2.4 Other types of AIE-nanoparticles for in vivo functional bioimaging 217

10.3 Multiphoton-Induced Fluorescence from AIE Dyes and Applications in

In Vivo Functional Microscopic Imaging 219

10.3.1 Two- and three-photon-induced fluorescence of AIE dyes 219

10.3.2 AIE dye-encapsulated nanomicelles for two-photon blood vessel imaging

of live mice 223

10.3.3 AIE dye-encapsulated nanomicelles for two-photon brain imaging

of live mice 226

10.4 Summary and Perspectives 228

Acknowledgments 230

References 230

11 Specific Light-Up Bioprobes with Aggregation-Induced Emission Characteristics for Protein Sensing 234

Jing Liang, Haibin Shi, Ben Zhong Tang, and Bin Liu

11.1 Introduction 234

11.2 In Vitro Detection of Integrin avb3 Using a TPS-Based Probe 235

11.2.1 Detection mechanisms 236

11.2.2 Synthesis and characterization of the TPS-2cRGD probe 236

11.2.3 Detection of integrin in solutions 238

11.2.4 In vitro sensing of integrin in cancer cells 239

11.3 Real-Time Monitoring of Cell Apoptosis and Drug Screening with a TPE-Based Probe 240

11.3.1 Design principles 240

11.3.2 Synthesis and characterization of Ac-DEVEK-TPE probe 241

11.3.3 Detection of caspase and kinetic study of caspase activities in solutions 242

11.3.4 Imaging of cell apoptosis and screening of apoptosis-inducing agents 243

11.4 In Vivo Monitoring of Cell Apoptosis and Drug Screening with PyTPE-Based Probe 246

11.4.1 Working principles 246

11.4.2 Synthesis and characterization of DEVD-PyTPE probe 247

11.4.3 Monitoring of caspase activities in solutions 248

11.4.4 In vitro and in vivo imaging of cell apoptosis 248

11.5 Conclusion 250

Acknowledgments 250

References 251

12 Applications of Aggregation-Induced Emission Materials in Biotechnology 254

Yuning Hong, Jacky W.Y. Lam, and Ben Zhong Tang

12.1 Introduction 254

12.2 AIE Materials for Nucleic Acid Studies 255

12.2.1 Quantitation and gel visualization of DNA and RNA 255

12.2.2 Specific probing of G-quadruplex DNA formation 257

12.3 AIE Materials for Protein Studies 258

12.3.1 Quantitation and PAGE staining of proteins 258

12.3.2 Fluorescence immunoassay by AIE materials 261

12.3.3 Monitoring of the unfolding/refolding process of human serum albumin 261

12.3.4 Monitoring and inhibition of amyloid fibrillation of insulin 262

12.4 AIE Materials for Live Cell Imaging 264

12.4.1 AIE bioprobes for long-term cell tracking 264

12.4.2 AIE nanoparticles for cell staining 264

12.5 Conclusion 266

References 267

Index 271