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Handbook of Aggregation-Induced Emission, Volume 2

Typical AIEgens Design
1. Aufl.

von: Youhong Tang, Ben Zhong Tang
201,99 €
Verlag:	Wiley
Format:	EPUB
Veröffentl.:	04.04.2022
ISBN/EAN:	9781119642961
Sprache:	englisch
Anzahl Seiten:	624

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Titelbeschreibung

The second volume of the ultimate reference on the science and applications of aggregation-induced emission The Handbook of Aggregation-Induced Emission explores foundational and advanced topics in aggregation-induced emission, as well as cutting-edge developments in the field, celebrating twenty years of progress and achievement in this important and interdisciplinary field. The three volumes combine to offer readers a comprehensive and insightful interpretation accessible to both new and experienced researchers working on aggregation-induced emission. In Volume 2: Typical AIEgens Design, the editors address the design and synthesis of typical AIEgens that have made significant contributions to aggregation-induced emission research. Recent advances in the development of aggregation-induced emission systems are discussed and the book covers novel aggregation-induced emission systems in small molecule organogels, polymersomes, metal-organic coordination complexes and metal nanoclusters. Readers will also discover: <ul> <li>A thorough introduction to the synthesis and applications of tetraphenylpyrazine-based AIEgens, AIEgens based on 9,10-distyrylanthracene , and the Salicylaldehyde Schiff base </li> <li>Practical discussions of aggregation-induced emission from the sixth main group and fluorescence detection of dynamic aggregation processes using AIEgens </li> <li>Coverage of cyclic triimidazole derivatives and the synthesis of multi-phenyl-substituted pyrrole based materials and their applications </li> </ul> Perfect for academic researchers working on aggregation-induced emission, this set of volumes is also ideal for professionals and students in the fields of photophysics, photochemistry, materials science, optoelectronic materials, synthetic organic chemistry, macromolecular chemistry, polymer science, and biological sciences.

Inhaltsverzeichnis

List of Contributors xvii Preface to Handbook of Aggregation-Induced Emission xxiii Preface to Volume 2: Typical AIEgens Design xxv 1 Tetraphenylpyrazine-based AIEgens: Synthesis and Applications 1 Ming Chen, Anjun Qin, and Ben Zhong Tang 1.1 Introduction 1 1.2 Synthesis of TPP-based AIEgens 3 1.2.1 Cyclization Reaction 3 1.2.2 Suzuki–Miyaura Reaction 7 1.3 Functionalities of TPP-based AIEgens 8 1.3.1 Organic Light-emitting Diodes 8 1.3.2 Fluorescent Sensors 9 1.3.3 Chiral Cage for Self-assembly to Achieve White-light Emission 13 1.3.4 Metal–organic Framework 15 1.4 Conclusion 17 References 18 2 AIEgens Based on 9,10-Distyrylanthracene (DSA): From Small Molecules to Macromolecules 23 Leijing Liu, Bin Xu, and Wenjing Tian 2.1 Introduction 23 2.2 Application of AIE Luminogens Based on 9,10-Distyrylanthracene 24 2.2.1 Smart Materials with Stimulus Response 24 2.2.1.1 Piezofluorochromic Materials 24 2.2.1.2 Photochromic Materials 27 2.2.1.3 Thermochromic Materials 27 2.2.1.4 Acidichromic Materials 27 2.2.1.5 Multistimuli-responsive Materials 30 2.2.2 High Solid-state Luminescent Materials 30 2.2.3 Fluorescent Materials for Bioimaging 35 2.2.4 Fluorescent Probes for Chemical and Biological Sensing 41 2.2.4.1 Fluorescent Probes for Chemical Sensing 41 2.2.4.2 Fluorescent Probes for Biological Sensing 44 2.3 Conclusions and Outlook 46 Acknowledgments 47 References 47 3 Typical AIEgens Design: Salicylaldehyde Schiff Base 53 Yue Zheng and Aijun Tong 3.1 Introduction 53 3.1.1 AIE and ESIPT of Salicylaldehyde Schiff Base 53 3.1.2 Universal Design of SSB-based AIEgens 55 3.2 Fluorescent Probes 55 3.2.1 Metal Ion Detection and Imaging 55 3.2.2 Biologically and Environmentally Related Molecular Detection and Imaging 63 3.2.3 Ratiometric pH Probes 76 3.2.4 Bioimaging 76 3.3 Fluorescent Materials 81 3.3.1 Solid Fluorescence Emitting and Stimuli-Responsive Materials 81 3.3.2 Nanoparticles 88 3.4 Summary and Perspectives 91 References 92 4 Diaminodicyanoquinodimethanes: Fluorescence Emission Enhancement in Aggregates and Solids 97 N. Senthilnathan and T. P. Radhakrishnan 4.1 Introduction 97 4.1.1 Molecular Materials 97 4.1.2 ‘Push–Pull’ Molecules 97 4.1.3 Diaminodicyanoquinodimethanes 98 4.2 Nonlinear Optical Materials based on DADQs 100 4.2.1 Molecular Hyperpolarizability 100 4.2.2 SHG Materials 100 4.2.3 Structure–Property Correlations 101 4.3 Enhanced Fluorescence in Aggregates and Solids Based on DADQs 102 4.3.1 Remote Functionalized Systems 102 4.3.2 Color Tuning, Nanocrystals, and Colloids 103 4.3.3 Ultrathin Films 105 4.3.4 New Directions 105 4.4 Mechanistic Insights into the Enhanced Fluorescence 106 4.4.1 Relevance of Intramolecular Effects 106 4.4.2 Role of Intermolecular Effects 106 4.5 Impact of Crystallinity on the Fluorescence Response 108 4.5.1 Amorphous-to-Crystalline Transformation: Fluorescence Switching and Tuning 108 4.5.2 Reversible Amorphous–Crystalline Transformations: Phase Change Materials 108 4.5.3 Impact of External Stimuli 110 4.6 Emergent and Potential Applications of DADQs 110 4.6.1 Electroluminescence and Nonlinear Optics 110 4.6.2 Bioimaging 110 4.6.3 Photoelectrochemical and Photobioelectrochemical Applications 112 4.6.4 Memory Devices 112 4.7 Concluding Remarks 113 Acknowledgements 114 References 114 5 Aggregation-induced Emission from the Sixth Main Group 119 Jan Balszuweit, Bibhisan Roy, and Jens Voskuhl 5.1 Introduction 119 5.2 Oxygen 119 5.2.1 Oxygen-Containing Heterocycles 120 5.2.2 Oxo-ether Containing AIE-Active Luminogens 122 5.3 Sulfur 126 5.3.1 Luminogens Based on Thiophenes 126 5.3.2 Thioethers with Aggregation-Induced Emission Properties 129 5.3.3 Emissive Sulfones 131 5.4 Selenium and Tellurium 132 5.4.1 Selenium-Containing Luminophores 132 5.4.2 Tellurium-Containing Luminophores 134 5.5 Conclusion 138 Acknowledgment 138 References 138 6 Fluorescence Detection of Dynamic Aggregation Processes Using AIEgens: Hexaphenylsilole and Cyanostilbene 143 Fuyuki Ito 6.1 Introduction 143 6.2 Selective Detection of Phase Transformation During Evaporative Crystallization of Hexaphenylsilole 145 6.3 Observation of the Initial Stage of Organic Crystal Formation During Solvent Evaporation Using a Cyanostilbene Derivative 149 6.4 Chemometrix Analysis of the Aggregated Structure of Cyanostilbene in a Reprecipitation Solution Using Fluorescence Excitation Spectroscopy 152 6.5 UV-triggered Fluorescence Enhancement of a Dicyanostilbene Derivative Film Cast from an Ethanol Solution 158 6.6 Concluding Remarks 162 Acknowledgments 162 References 162 7 Cyclic Triimidazole Derivatives: An Intriguing Family of Multifaceted Emitters 165 Elena Cariati, Elena Lucenti, Andrea Previtali, and Alessandra Forni 7.1 Introduction 165 7.2 The Protoype: Cyclic Triimidazole 166 7.3 Halogenated Derivatives of Cyclic Triimidazole 175 7.3.1 Bromine Derivatives 176 7.3.2 Iodine Derivatives 179 7.4 Organic Derivatives 184 7.4.1 2-Fluoropyridine Derivative 185 7.4.2 Tribenzoimidazole Derivative 186 7.5 Hybrid Inorganic/Organic Derivatives 188 7.6 Conclusions 191 Acknowledgments 191 References 191 8 Synthesis of Multi-phenyl-substituted Pyrrole (MPP)-based AIE Materials and Their Applications 195 Zhengxu Cai, Yunxiang Lei, and Yuping Dong 8.1 Introduction 195 8.2 Modular Approach: Systematic Synthesis of MPPs 196 8.3 Structures and Photophysical Properties 198 8.4 Applications of MPP-based Materials 204 8.4.1 Chemical/Biological Sensing 204 8.4.2 Multi-stimulus Response Materials 208 8.4.3 Optoelectronic Systems 210 8.4.4 Biological Application 213 8.5 Conclusion and Outlook 216 References 216 9 Development of a New Class of AIEgens: Tetraarylpyrrolo [3,2-b] Pyrroles (TAPPs) 221 Vishal G. More, Ratan W. Jadhav, Mohammad Al Kobaisi, Lathe A. Jones, and Sheshanath V. Bhosale 9.1 Introduction 221 9.2 The Accidental Discovery of TAPP 223 9.3 Synthesis of TAPP 223 9.4 Possible Mechanism of TAPP Synthesis 227 9.5 Reactivity of TAPP 228 9.6 π-Expansion of TAPP 229 9.7 π-Expanded 1,4-dihydropyrrolo[3,2-b] pyrrole 231 9.8 Photophysical Optical Properties of TAPP 239 9.9 Conclusion and Outlook 245 Acknowledgments 247 References 247 10 Small Molecule Organogels from AIE Active α-Cyanostilbenes 255 Jagadish Katla, Beena Kumari, and Sriram Kanvah 10.1 Introduction 255 10.2 Organogels with Trifluoromethyl Substitution 256 10.3 Organogels with Chiral Units/Chiral Hosts 260 10.4 Stimuli–Responsive Organogels 262 10.5 Organogels with Sensing Applications 266 10.6 Concluding Remarks 271 Acknowledgments 271 References 271 11 Stimuli-responsive Pure Organic Luminescent Supramolecules 277 Siyu Sun and Xiang Ma 11.1 Introduction 277 11.2 Pure Organic Fluorescent Supramolecules 280 11.2.1 Pure Organic Fluorescent Supramolecules Containing Macrocycles 280 11.2.1.1 Pure Organic Fluorescent Supramolecules Containing Cyclodextrins 280 11.2.1.2 Pure Organic Fluorescent Supramolecules Containing Calixarenes 284 11.2.1.3 Pure Organic Fluorescent Supramolecules Containing Cucurbiturils 284 11.2.1.4 Pure Organic Fluorescent Supramolecules Containing Pillararene 288 11.2.1.5 Pure Organic Fluorescent Supramolecules Containing Crown Ether 290 11.2.2 Pure Organic Fluorescent Supramolecules Without Macrocycles 291 11.3 Pure Organic Phosphorescent Supramolecules 293 11.3.1 Pure Organic Phosphorescent Supramolecules Based on Macrocyclic Molecules 293 11.3.1.1 Pure Organic Phosphorescent Supramolecules Containing Cyclodextrin 293 11.3.1.2 Pure Organic Phosphorescent Supramolecules Containing Cucurbiturils 297 11.3.1.3 Pure Organic Phosphorescent Supramolecules Containing Calixarenes 297 11.3.1.4 Pure Organic Phosphorescent Supramolecules Containing Crown Ether 297 11.3.2 Pure Organic Phosphorescent Supramolecules Without Macrocyclic Molecules 299 11.3.2.1 Pure Organic Supramolecular Phosphorescence System With Doping-Based Host–Guest Interaction 299 11.3.2.2 Other Pure Organic Phosphorescent Supramolecules 301 11.4 Conclusions 306 Acknowledgments 306 References 307 12 AIE Fluorescent Polymersomes 311 Hui Chen and Min-Hui Li 12.1 Introduction 311 12.2 Structural Consideration of Block Copolymers for Polymersome Formation 314 12.3 Methods of Polymersome Preparation 315 12.4 Techniques of Polymersome Characterization 317 12.5 AIE Polymersomes Based on PEG-b-POSS 317 12.6 AIE Polymersomes Based on Amphiphilic Polypeptoids 319 12.7 AIE Polymersomes Based on PEG-b-Polycarbonate 321 12.8 AIE Polymersomes Based on Amphiphilic Polynorbornene 323 12.9 AIE Polymersomes Based on Amphiphilic Block Copolymers by RAFT Polymerization 326 12.10 Summary and Perspectives 330 References 334 13 Designs for AIE Molecules and Functional Luminescent Materials Based on Boron-containing Element-blocks 341 Kazuo Tanaka, Masayuki Gon, Shunichiro Ito, and Yoshiki Chujo 13.1 Introduction 341 13.1.1 Generals of Commodity Luminescent Boron Complexes 341 13.1.2 Trends in the Development of Advanced Organic Electronic Devices 342 13.1.3 Strategies for Obtaining Solid-state Luminescence and Stimuli-responsiveness 343 13.1.4 New Ideas for Material Design Based on “Element-blocks” 343 13.2 Solid-state Luminescence and Luminochromism of o-Carboranes 344 13.2.1 Emission Mechanism of Aryl-modified o-Carboranes 344 13.2.2 AIE Behavior of o-Carborane Materials 344 13.2.3 Formation of Twisted Intramolecular Charge Transfer (TICT) State in the Crystalline State of o-Carboranes 346 13.2.4 Thermochromic Luminescence of o-Carboranes 346 13.2.5 Intense Solid-state Luminescent Molecules 347 13.2.6 Solid-state Excimer Emission 348 13.3 Boron Complexes with β-Ketimine and β-Diketimine Ligands 349 13.3.1 Generals of Boron Ketiminates and Diketiminates 349 13.3.2 Unique Solid-state Luminescent Properties of Conjugated Boron Complexes 350 13.3.3 Thermally Stable Mechanochromic Luminescent Hybrid with the Siloxane Unit 350 13.3.4 Luminescent Properties of β-Diketiminate Complexes 352 13.3.5 AIE-active Conjugated Polymers 352 13.3.6 Design for Film-type Sensors 353 13.3.7 Sensitive Luminochromic Sensors with Gallium Complexes 354 13.4 Rational Design for AIE-active Molecules Based on “Flexible” Boron Complexes 355 13.4.1 Concept for Rational Design 355 13.4.2 Ring-fused or Nonring-fused Molecules 355 13.4.3 Thermosalient-active Molecules 357 13.4.4 Solid-state Luminescent π-Conjugated Polymer 358 13.5 Conclusion 359 References 359 14 Aggregation-induced Emission (AIE) Active Metal–Organic Coordination Complexes 367 Xueliang Shi, Xuzhou Yan, and Hai-Bo Yang 14.1 Introduction 367 14.2 Conception and Design Strategy 368 14.3 AIE Active Metallacycles 371 14.3.1 AIE Active Simple Metallacycles 371 14.3.2 AIE Active Fused Metallacycles 378 14.3.3 AIE Active Metallacycle Polymers 382 14.4 AIE Active Metallacages 389 14.5 AIE Active Metal–organic Frameworks (MOFs) 397 14.6 Summary and Outlook 405 Acknowledgments 406 References 406 15 AIE-type Luminescent Metal Nanoclusters 411 Zhennan Wu, Qiaofeng Yao, and Jianping Xie 15.1 Introduction 411 15.2 In the “Single-cluster” Scenario 412 15.2.1 AIE-type Luminescent Metal NCs 412 15.2.2 Atomically Precise AIE-type Luminescent Metal NCs 416 15.2.3 Approaches to Luminescence Enhancement of Metal NCs in the Scheme of AIE 418 15.2.3.1 Surface Engineering 418 15.2.3.2 Roles of the Core 422 15.3 Beyond the “Single-cluster” Scenario 423 15.3.1 Poor-solvent-induced AIE of Metal NCs 423 15.3.2 Ion-induced AIE of Metal NCs 423 15.3.3 Supramolecular Interactions Induced AIE of Metal NCs 426 15.3.4 Spatial Confinement-induced AIE of Metal NCs 429 15.4 Application of the AIE-type Luminescent Metal NCs 433 15.4.1 Chemical Sensing 433 15.4.2 Biological Applications 434 15.4.3 Photosensitizer 434 15.4.4 Light-emitting Diodes (LEDs) 434 15.5 Conclusion and Outlook 436 References 437 16 Aggregation-induced Emission in Coinage Metal Clusters 443 Shuang-Quan Zang and Kai Li 16.1 Introduction 443 16.2 AIE-active Gold Cluster 444 16.3 AIE-active Silver Cluster 450 16.4 AIE-active Copper Cluster 454 16.5 AIE-active Bimetallic Cluster 462 16.6 Conclusions 465 References 466 17 Activated Alkynes in Metal-free Bioconjugation 471 Xianglong Hu and Ben Zhong Tang 17.1 Introduction 471 17.2 Alkyne–Azide-based Bioconjugation 472 17.3 Activated Alkyne–Amine-based Bioconjugation 473 17.4 Activated Alkyne–Thiol-based Bioconjugation 480 17.5 Activated Alkyne–Hydroxyl-based Bioconjugation 483 17.6 Activated Alkyne-based Bioconjugation and Polymerization in Living Cells and Pathogens 484 17.7 Conclusion 488 References 488 18 AIE-active BODIPY Derivatives 493 Yali Liu, Yuzhang Huang, Rongrong Hu, and Ben Zhong Tang 18.1 Introduction 493 18.2 Structures of BODIPY Derivatives 495 18.2.1 BODIPY Derivatives Without Other Chromophore 495 18.2.2 TPE-containing BODIPYs 496 18.2.3 TPA-containing BODIPYs 498 18.2.4 Benzodithiophene-containing BODIPYs 499 18.2.5 Chiral BODIPYs 500 18.2.6 Metal-containing BODIPYs 502 18.2.7 BODIPY-containing Polymers 503 18.2.8 Other BODIPY Derivatives 504 18.3 Structural–property Relationship 508 18.3.1 Conjugation Effect 508 18.3.2 Number and Position of Substitutes 508 18.3.3 Substitution Group 513 18.3.4 Alkyl Substitutes on BODIPY Core 516 18.3.5 AIEgens Attached Through Nonconjugated Spacers 518 18.3.6 Other Substitution Structures 519 18.4 Application 522 18.4.1 Chemosensor 522 18.4.2 Bioimaging 526 18.5 Conclusion 532 References 532 19 Photochemistry-regulated AIEgens and Their Applications 537 Xia Ling and Meng Gao 19.1 Introduction 537 19.2 Photocleavage Reaction 537 19.3 Photoreduction Reaction 539 19.4 Photocyclodehydrogenation Reaction 540 19.5 Photooxidative Dehydrogenation Reaction 543 19.6 Spiropyran-merocyanine Reversible Conversion 544 19.7 Dithienylethene-based Ring-open/-closing Reaction 545 19.8 Enol–Keto Isomerization Reaction 550 19.9 E/Z Isomerization Reaction 552 19.10 Photo-induced [2 + 2] Cycloaddition 554 19.11 Combinational Photoreactions 554 19.12 Conclusion and Outlook 556 References 556 20 Design and Development of Naphthalimide Luminogens 559 Niranjan Meher and Parameswar Krishnan Iyer 20.1 Introduction 559 20.2 Naphthalimides with N-Functionalization (I) 564 20.3 Naphthalimides Substituted at the 4th Position with Oxygen Atom (II) 567 20.4 Naphthalimides Substituted at the 4th Position with Nitrogen Atom (III) 570 20.5 Naphthalimides with C−C Aromatic Substitution (IV) 571 20.6 Naphthalimides with C−C Double-and Triple-Bond Substitutions (V and VI) 574 20.7 Naphthalimides with the Significant Role of Multifunctionalization (VII) 576 20.8 Conclusion and Outlooks 580 References 581 Index 587

Autorenportrait

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.

Back cover copy

The second volume of the ultimate reference on the science and applications of aggregation-induced emission The Handbook of Aggregation-Induced Emission explores foundational and advanced topics in aggregation-induced emission, as well as cutting-edge developments in the field, celebrating twenty years of progress and achievement in this important and interdisciplinary field. The three volumes combine to offer readers a comprehensive and insightful interpretation accessible to both new and experienced researchers working on aggregation-induced emission. In Volume 2: Typical AIEgens Design, the editors address the design and synthesis of typical AIEgens that have made significant contributions to aggregation-induced emission research. Recent advances in the development of aggregation-induced emission systems are discussed and the book covers novel aggregation-induced emission systems in small molecule organogels, polymersomes, metal-organic coordination complexes and metal nanoclusters. Readers will also discover: <ul><li>A thorough introduction to the synthesis and applications of tetraphenylpyrazine-based AIEgens, AIEgens based on 9,10-distyrylanthracene, and the Salicylaldehyde Schiff base</li> <li>Practical discussions of aggregation-induced emission from the sixth main group and fluorescence detection of dynamic aggregation processes using AIEgens</li> <li>Coverage of cyclic triimidazole derivatives and the synthesis of multi-phenyl-substituted pyrrole based materials and their applications</li></ul> Perfect for academic researchers working on aggregation-induced emission, this set of volumes is also ideal for professionals and students in the fields of photophysics, photochemistry, materials science, optoelectronic materials, synthetic organic chemistry, macromolecular chemistry, polymer science, and biological sciences.