Handbook of Aggregation-Induced Emission, Volume 3

Youhong Tang is a Professor at Flinders University, Australia and actively works in aggregation-induced emission areas. Ben Zhong Tang is a Chair Professor at the Chinese University of Hong Kong, Shenzhen. He is widely known as the pioneer of the study of aggregation-induced emission.

List of Contributors xv

Preface xxi

Preface to Volume 3: Applications xxiii

1 AIE-active Emitters and Their Applications in OLEDs 1
Qiang Wei, Jiasen Zhang, and Ziyi Ge

1.1 Introduction 1

1.2 Conventional Aggregation-induced Emissive Emitters 4

1.2.1 Blue Aggregation-induced Emissive Emitters 4

1.2.2 Green Aggregation-induced Emissive Emitters 7

1.2.3 Red Aggregation-induced Emissive Emitters 8

1.2.4 Aggregation-induced Emission-active Emitters-Based White OLED 9

1.3 High Exciton Utilizing Efficient Aggregation-induced Emissive Materials 13

1.3.1 Aggregation-induced Phosphorescent Emissive Emitters 13

1.3.2 Aggregation-induced Delayed Fluorescent Emitters 14

1.3.3 Hybridized Local and Charge Transfer Materials Aggregation-induced Emissive Emitters 15

1.4 Conclusion and Outlook 16

References 18

2 Circularly Polarized Luminescence of Aggregation-induced Emission Materials 27
Fuwei Gan, Chengshuo Shen, and Huibin Qiu

2.1 Introduction of Circularly Polarized Luminescence 27

2.2 Small Organic Molecules 28

2.3 Macrocycles and Cages 33

2.4 Metal Complexes and Clusters 35

2.5 Supramolecular Systems 37

2.6 Polymers 46

2.7 Liquid Crystals 50

2.8 Conclusions and Outlook 51

References 53

3 AIE Polymer Films for Optical Sensing and Energy Harvesting 57
Andrea Pucci

3.1 Introduction 57

3.2 Working Mechanism of AIEgens 59

3.3 AIE-doped Polymer Films for Optical Sensing 61

3.3.1 Mechanochromic AIE-doped Polymer Films 61

3.3.2 Thermochromic AIE-doped Polymer Films 65

3.3.3 Vapochromic AIE-doped Polymer Films 67

3.4 AIE-doped Polymer Films for Energy Harvesting 70

3.5 Conclusions 72

References 73

4 Aggregation-induced Electrochemiluminescence 79
Serena Carrara

4.1 Introduction: From Electrochemiluminescence to AI-ECL 79

4.1.1 Mechanisms of AI-ECL 81

4.2 Classification and Properties of AI-ECL luminophores 85

4.2.1 Metal Transition Complexes 85

4.2.2 Polymers and Polymeric Nanoaggregates 87

4.2.3 Organic Molecules 90

4.2.4 Hybrid and Functional Materials 93

4.3 Applications and Outlooks 95

References 98

5 Mechanoluminescence Materials with Aggregation-induced Emission 105
Zhiyong Yang, Juan Zhao, Eethamukkala Ubba, Zhan Yang, Yi Zhang, and Zhenguo Chi

5.1 Introduction 105

5.2 Mechanoluminescence of Organic Molecules Not Mentioned AIE 107

5.3 ML–AIE Materials 117

5.4 Summary and Outlook 132

References 133

6 Dynamic Super-resolution Fluorescence Imaging Based on Photo-switchable Fluorescent Spiropyran 139
Cheng Fan, Chong Li, and Ming-Qiang Zhu

6.1 Introduction 139

6.2 Materials and Methods 141

6.2.1 Materials 141

6.2.2 The Preparation of PSt-b-PEO Block Copolymer Micelles 141

6.2.3 Super-resolution Microscope 141

6.2.4 Super-resolution Imaging 141

6.3 Super-resolution Imaging of Block Copolymer Self-assembly 141

6.4 Optimization of Spatial Resolution 144

6.5 Temporal Resolution 145

6.6 Dynamic Super-resolution Imaging 147

6.7 Conclusion and Prospection 147

References 149

7 Visualization of Polymer Microstructures 151
Shunjie Liu, Yuanyuan Li, Ting Han, Jacky W. Y. Lam, and Ben Zhong Tang

7.1 Introduction 151

7.2 Synthetic Polymers 152

7.2.1 Polymer Self-assembly 152

7.2.2 Polymerization Reaction 154

7.2.3 Physical Process Visualization 155

7.2.3.1 Glass Transition Temperature 155

7.2.3.2 Solubility Parameter 157

7.2.3.3 Crystallization 158

7.2.3.4 Microphase Separation 158

7.2.4 Stimuli Response 161

7.2.4.1 Heat Response 161

7.2.4.2 Humidity Response 162

7.2.4.3 Other Response 164

7.3 Biological Polymers 164

7.3.1 DNA Synthesis 165

7.3.2 DNA Sequence 165

7.3.3 Protein Conformation 168

7.3.4 Protein Fibrillation 169

7.3.5 Other Process 171

7.4 Summary and Perspective 172

References 173

8 Self-assembly of Aggregation-induced Emission Molecules into Micelles and Vesicles with Advantageous Applications 179
Jinwan Qi, Jianbin Huang, and Yun Yan

8.1 General Background of Micelles and Vesicles 179

8.2 AIE Micelles 180

8.2.1 General Strategies Leading to AIE Micelles 180

8.2.1.1 Incorporating Tetraphenylethylene (TPE) Unit into Single-Chained Surfactants 180

8.2.1.2 Incorporating Tetraphenylethylene (TPE) Unit into Gemini Surfactants 182

8.2.1.3 Incorporating Platinum Complex into Amphiphiles 182

8.2.1.4 Polymeric AIE Micelles 183

8.2.1.5 Coassembled AIE Micelles 188

8.2.2 Applications of AIE Micelles 190

8.2.2.1 Untargeted Bioimaging 191

8.2.2.2 Targeted Bioprobing 192

8.2.2.3 Micellar Theranostics 193

8.2.2.4 Sensing 197

8.2.2.5 Visualization of Physical Chemistry Process 199

8.3 AIE Vesicles 203

8.3.1 AIE Vesicles Based on Synthetic Amphiphiles 203

8.3.1.1 Synthetic Ionic Amphiphiles 203

8.3.1.2 Synthetic Nonionic AIE Amphiphiles 203

8.3.1.3 Synthetic Nonamphiphilic AIE Molecules 205

8.3.2 Supramolecular AIE Vesicles 206

8.3.2.1 AIE Vesicles Directed by Host–Guest Chemistry 208

8.3.2.2 AIE Vesicles Based on Electrostatic Interactions 209

8.3.2.3 AIE Vesicles Based on Coordination Interactions 209

8.3.3 Applications of AIE Vesicles 210

8.3.3.1 Cell Models 210

8.3.3.2 Bioimaging 211

8.3.3.3 Theranostics 212

8.3.3.4 Light-harvesting 214

8.3.3.5 Other Applications 216

8.4 Summary and Outlooks 217

References 217

9 Vortex Fluidics-mediated Fluorescent Hydrogels with Aggregation-induced Emission Characteristics 221
Javad Tavakoli and Youhong Tang

9.1 Introduction 221

9.2 Tunning the Size and Property of AIEgens, a New Approach to Create FL Hydrogels with Superior Properties 222

9.3 AIEgens for Characterization of Hydrogels 231

9.4 Conclusion 238

References 238

10 Design and Preparation of Stimuli-responsive AIE Fluorescent Polymers-based Probes for Cells Imaging 243
Juan Qiao and Li Qi

10.1 Introduction 243

10.2 Design and Preparation Strategies for AIE–SRP Probes 246

10.2.1 Mechanism of AIE–SRP Probes 246

10.2.2 Stimuli-Responsive Polymers 247

10.2.2.1 Thermal-Sensitive Polymers 247

10.2.2.2 pH-Sensitive Polymers 247

10.2.2.3 Photo-Sensitive polymers 247

10.2.2.4 Protein-Sensitive Polymers 248

10.2.3 AIE Dyes 249

10.2.4 Combination of Stimuli-Sensitive Polymer and AIE Dyes 251

10.2.4.1 Chemical Synthesis 251

10.2.4.2 Physical Blending 256

10.3 Application of AIE–SRP Probes 257

10.3.1 Thermal-Sensitive Application 257

10.3.2 pH-Sensitive Application 259

10.3.3 Photo-Sensitive Application 260

10.3.4 Protein-Sensitive Application 260

10.3.5 MultiSensitive Application 260

10.4 Summary and Prospect 262

References 263

11 AIE: New Strategies for Cell Imaging and Biosensing 269
Tracey Luu, Bicheng Yao, and Yuning Hong

11.1 Introduction 269

11.2 Cellular Imaging 271

11.2.1 Cytoplasma Membrane Imaging 272

11.2.2 Mitochondria Imaging 273

11.2.3 Lysosome Imaging 275

11.2.4 Lipid Droplet Imaging 276

11.2.5 Nucleus Imaging 277

11.3 Biosensing 278

11.3.1 Ions 279

11.3.2 Lipids and Carbohydrates 281

11.3.3 Amino Acids, Proteins, and Enzymes 283

11.3.4 Nucleic Acids and Pathogens 286

11.4 Conclusion 289

References 289

12 AIE-based Systems for Imaging and Image-guided Killing of Pathogens 297
Jiangman Sun, Fang Hu, Yongjie Ma, Yufeng Li, Guan Wang, and Xinggui Gu

12.1 Introduction 297

12.2 Bacteria Imaging Based on AIEgens 298

12.2.1 Broad-spectrum Bacterial Imaging and Identification 299

12.2.2 Gram Positive and Gram Negative Bacteria Distinguishing 299

12.2.3 Long-term Bacterial Tracking 303

12.2.4 Live and Dead Bacteria Discrimination Based on AIEgens 304

12.3 Bacteria-targeted Imaging and Ablation Based on AIEgens 305

12.3.1 Surfactant-structure Based AIEgens for Bacterial Elimination 305

12.3.2 Photodynamic Therapy for Bacterial Elimination 309

12.3.2.1 Vancomycin-bacteria Interaction Mediated Photodynamic Ablation 309

12.3.2.2 Positive-charged AIE PS for Bacteria Ablation 311

12.3.2.3 Metabolic Labeling-mediated Imaging and Photodynamic Ablation 313

12.3.3 AIEgen with Antimicrobial Agents for Bacteria Elimination 315

12.3.4 Biodegradable Biocides for Bacteria Elimination 315

12.4 Bacterial Susceptibility Evaluation and Antibiotics Screening 315

12.5 Sensors for Bacterial Detection Based on AIEgens 317

12.5.1 Fluorescent Sensor Arrays 317

12.5.2 Biosensors Constructed by Electrospun Fibers 319

12.5.3 Micromotors for Bacterial Detection 320

12.6 Conclusions and Perspectives 321

References 321

13 AIEgen-based Trackers for Cancer Research and Regenerative Medicine 329
Chen Zhang and Kai Li

13.1 Introduction 329

13.2 AIEgens for Long-term Cancer Cell Tracking 330

13.2.1 AIEgen-based Long-term Cell Trackers with Emission in the Visible Range 330

13.2.2 AIEgen-based Long-term Cell Trackers with Near-infrared (NIR) Emission 334

13.2.3 AIEgen-based Long-term Cell Trackers with Multiphoton Absorption 335

13.2.4 AIEgen-based Hybrid or Multifunctional Systems for Cell Tracking 336

13.3 AIEgens for Stem Cell-based Regenerative Medicine and Regeneration-related Process 338

13.3.1 AIEgen-based Trackers for Adipose-derived Stem Cells 338

13.3.2 AIEgen-based Trackers for Bone Marrow Stem Cells 340

13.3.3 AIEgen-based Trackers for Embryo-related Cells 342

13.3.4 AIEgens for Monitoring Biological Process in Regenerative Medicine 345

13.3.5 AIEgen-based Nanocomplexes in Regenerative Medicine 346

13.4 Conclusion 347

References 350

14 AIE-active Fluorescence Probes for Enzymes and Their Applications in Disease Theranostics 355
Jianguo Wang and Guoyu Jiang

14.1 Introduction 355

14.2 AIE-active Fluorescence Probes for Enzymes and Their Applications in Disease Theranostics 356

14.2.1 AIE-active Fluorescence Probes for Alkaline Phosphatase 356

14.2.2 AIE-active Fluorescence Probes for Caspases 358

14.2.3 AIE-active Fluorescence Probes for Cathepsin B 361

14.2.4 AIE-active Fluorescence Probes for β-Galactosidase 363

14.2.5 AIE-active Fluorescence Probes for γ-Glutamyltranspeptidase 365

14.2.6 AIE-active Fluorescence Probes for Reductases 366

14.2.6.1 AIE-active Fluorescence Probes for AzoR 366

14.2.6.2 AIE-active Fluorescence Probes for NQO1 369

14.2.6.3 AIE-active Fluorescence Probes for NTR 369

14.2.6.4 AIE-active Fluorescence Probes for CYP450 Reductase 371

14.2.7 AIE-active Fluorescence Probes for Chymase 371

14.2.8 AIE-active Fluorescence Probes for Esterase 372

14.2.8.1 AIE-active Fluorescence Probes for CaE 372

14.2.8.2 AIE-active Fluorescence Probes for Lipase 375

14.2.9 AIE-active Fluorescence Probes for Histone Deacetylase 376

14.2.10 AIE-active Fluorescence Probes for MMP-2 379

14.2.11 AIE-active Fluorescence Probes for Furin 380

14.2.12 AIE-active Fluorescence Probes for Trypsin 380

14.2.13 AIE-active Fluorescence Probes for Telomerase 385

14.2.14 AIE-active Fluorescence Probes for DPP-4 386

14.3 Summary and Outlook 387

References 388

15 AIE Nanoprobes for NIR-II Fluorescence In Vivo Functional Bioimaging 399
Zhe Feng, Xiaoming Yu, and Jun Qian

15.1 Introduction 399

15.2 NIR-II Fluorescence Macroimaging In Vivo 400

15.3 NIR-II Fluorescence Wide-field Microscopic Imaging In Vivo 436

15.4 NIR-II Fluorescence Confocal Microscopic Imaging In Vivo 440

15.5 Summary and Perspectives 441

References 444

16 In Vivo Phototheranostics Application of AIEgen-based Probes 447
Zhiyuan Gao, Heqi Gao, and Dan Ding

16.1 Introduction 447

16.2 AIE Fluorescent Probe with Photodynamic Therapy Function 448

16.3 AIE Photoacoustic Probe with Photothermal Therapy Function 451

16.4 Application of AIE Fluorescent Probe in Synergistic Therapy 454

16.5 AIE Fluorescent Probe with Immunotherapy Function 458

16.6 Conclusions and Perspectives 460

References 460

17 Red-emissive AIEgens Based on Tetraphenylethylene for Biological Applications 465
Yanyan Huang, Fang Hu, and Deqing Zhang

17.1 Introduction 465

17.2 TPE-based AIEgens with Dicyanovinyl Group 466

17.2.1 Design of Red-emissive AIEgens with Dicyanovinyl Group 466

17.2.2 Red-emissive AIEgens as Photosensitizers 469

17.2.3 Photosensitization Enhancement of AIEgens with Dicyanovinyl Group 471

17.2.4 Self-assembly of AIEgens with Dicyanovinyl Groups 473

17.3 Pyridinium-based AIEgens 475

17.3.1 Photophysical Properties of Pyridinium-based AIEgens 475

17.3.2 Bio-sensing Applications of Pyridinium-substituted Tetraphenylethylenes 477

17.3.3 Bacterial Imaging and Ablation 479

17.3.4 Imaging and Interrupting Mitochondria and Related Biological Processes with Pyridinium-based AIEgens 480

17.4 Summary and Perspectives 485

References 485

18 Smart Luminogens for the Detection of Organic Volatile Contaminants 491
Niranjan Meher and Parameswar Krishnan Iyer

18.1 Introduction 491

18.2 Smart AIE Nanomaterials and their Sensing Applications for OVCs 493

18.2.1 Organic Framework 493

18.2.2 Molecular Rotors 499

18.2.3 Other Small Molecule 502

18.3 Summary and Outlook 506

References 506

19 Bulky Hydrophobic Counterions for Suppressing Aggregation-caused Quenching of Ionic Dyes in Fluorescent Nanoparticles 511
Ilya O. Aparin, Nagappanpillai Adarsh, Andreas Reisch, and Andrey S. Klymchenko

19.1 Introduction 511

19.2 Counterion Effect in Nanomaterials Based on Conventional Bright Fluorophores 513

19.3 Counterions and Aggregation-induced Emission 516

19.3.1 Counterion Effect in AIE Dyes 517

19.3.2 Ionic AIE: Lighting Up Environment-sensitive Ionic Dyes in Nanomaterials 519

19.4 Dye-loaded Polymeric NPs and the Crucial Role of Bulky Counterions 523

19.4.1 Principle 523

19.4.2 The Role of the Polymer 525

19.4.3 The Role of the Counterion 525

19.4.4 Dye Nature 528

19.4.5 Energy Transfer, Collective Behavior of Dyes and Biosensing 531

19.5 Conclusions 532

References 534

20 Fluorescent Silver Staining Based on a Fluorogenic Ag+ Probe with Aggregation-induced Emission Properties 541
Chuen Kam, Sheng Xie, Alex Y. H. Wong, and Sijie Chen

20.1 Introduction 541

20.2 Historical Background of Silver Staining 541

20.2.1 Silver Staining for Neurological Studies 542

20.2.2 Silver Staining from Neuroscience to Proteomics 544

20.3 Conventional Silver Staining Methods 544

20.4 Fluorogenic Probes for Ag+ Detection 546

20.5 Fluorogenic Silver Staining in Polyacrylamide Gel 550

20.6 Concluding Remarks 554

References 554

Index 559