Handbook of Aggregation-Induced Emission, Volume 3

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