Dynamic covalent chemistry: principles, reactions, and applications
Gespeichert in:
| Weitere Verfasser: | , |
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| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Hoboken, NJ, USA ; Chichester, West Sussex, UK
Wiley
2018
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| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis Klappentext |
| Beschreibung: | xvi, 441 Seiten Illustrationen, Diagramme (teilweise farbig) |
| ISBN: | 9781119075639 |
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| 245 | 1 | 0 | |a Dynamic covalent chemistry |b principles, reactions, and applications |c edited by Wei Zhang (Department of Chemistry and Biochemistry, University of Colorado, USA), Yinghua Jin (Department of Chemical and Biological Engineering and Department of Chemistry and Biochemistry, University of Colorado, USA) |
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Datensatz im Suchindex
| _version_ | 1804178135094132736 |
|---|---|
| adam_text | Contents
/
Preface xi
List of Contributors xv
1 Principles of Dynamic Covalent Chemistry 1
Fredrik Schaufelberger, Brian JJ. Timmer, and OlofRamstrom
1.1 Introduction 1
1.1.1 What is Dynamic Covalent Chemistry? 1
1.1.2 Importance of Dynamic Covalent Chemistry 3
1.1.3 Basic Concepts 3
1.2 The Dynamic Covalent Bond 5
1.2.1 Requirements for Dynamic Covalent Bonds 5
1.2.2 Catalysis of Exchange 6
1.2.3 Halting Equilibration 6
1.2.4 Exchange Symmetry 7
1.2.5 Methods to Confirm Reversibility 8
1.3 Dynamic Covalent Reactions 9
1.3.1 Dynamic Polar Reactions 9
1.3.1.1 C-N Bonds 9
1.3.1.2 C-C Bonds 12
1.3.1.3 C-O Bonds 17
1.3.1.4 C-S Bonds 18
1.3.1.5 S-S Bonds and Se-Se Bonds 20
1.3.1.6 B-O Bonds 21
1.3.1.7 N-X Bonds 22
1.3.2 Other Dynamic Reaction Types 22
1.3.2.1 Dynamic Covalent Pericyclic Reactions 22
1.3.2.2 Dynamic Covalent Radical Reactions 25
1.4 Conclusions 26
References 26
2 Dynamic Combinatorial Libraries 31
David Komaromy, Piotr Nowak, and Sijbren Otto
2.1 Introduction 31
2.1.1 A Short History of DCLs 31
2.1.2 Terminology 33
vi
Contents
2.1.3 Theoretical Considerations 34
2.2 Template-controlled DCLs 40
2.2.1 Receptors for Small Molecules and Ions 40
2.2.1.1 Inorganic Cations 40
2.2.1.2 Inorganic Anions 44
2.2.1.3 Biologically Relevant Small Molecules 45
2.2.1.4 Miscellaneous Organic Molecules 47
2.2.2 Ligands for Biomolecules 51
2.2.2.1 Protein Inhibitors 51
2.2.2.2 Nucleic Acids 55
2.2.3 Catalysis 57
2.2.4 Self/Cross-templating and Replicators 58
2.2.5 Interlocked Structures from DCLs 61
2.2.6 Folding 64
2.3 Controlling DCLs by Physical Means 68
2.3.1 Solvent Environment 70
2.3.2 Light 70
2.3.3 Temperature 72
2.3.4 Mechanical Force 72
2.4 Multiphase DCLs 73
2.4.1 Multiple Liquid Phases 73
2.4.2 Transport 75
2.4.3 Amphiphiles 73
2.4.4 Surface-liquid Interfaces 79
2.4.4.1 Resins 79
2.4.4.2 Nanoparticles 79
2.4.4.3 Flat Surfaces 80
2.4.5 Kinetically Controlled Phase Transfer 82
2.5 Other Applications of DCLs 86
2.5.1 Information Acquisition and Processing 86
2.5.2 Self-synthesizing Materials 90
2.6 Non-equilibrium DCLs 91
2.7 Analysis of DCLs 95
2.7.1 Liquid and Gas Chromatography 96
2.7.2 Mass Spectrometry 97
2.7.3 NMR Spectroscopy 99
2.7.4 Optical Spectroscopy 100
2.7.5 Microscopy Techniques 101
2.7.6 Diffraction and Scattering Techniques 102
2.7.7 Calculations 103
2.8 Conclusions and Outlook 103
References 105
3 Shape-persistent Macrocycles through Dynamic Covalent Reactions 121
Chao Yu, YinghuaJin, and Wei Zhang
3.1 Introduction and Importance of Shape-persistent Macrocycles 121
3.2 Thermodynamic Approach vs. Kinetic Approach 122
Contents
vii
3.3 Macrocycles through Alkyne Metathesis 123
3.3.1 Monomer-to-Macrocycle Strategy 123
3.3.1.1 Homo-sequenced Symmetrical Macrocycles 123
3.3.1.2 Hetero-sequenced Macrocycles 130
3.3.2 Mechanism Study of the Cyclooligomerization Process 134
3.3.3 Polymer-to-Macrocycle Strategy 135
3.4 Macrocycles through Imine Metathesis 138
3.4.1 Salphen-containing Macrocycles 138
3.4.1.1 Synthesis 138
3.4.1.2 Coordination with Metal Ions 140
3.4.2 Other Imine-linked Macrocycles 146
3.5 Macrocycles through Olefin Metathesis 150
3.6 Macrocycles through Boronate Ester Formation 151
3.7 Macrocycles through Orthogonal Dynamic Covalent Reactions 151
3.8 Conclusions and Outlook 155
References 156
4 Organic Cages through Dynamic Covalent Reactions 165
Huimin Ding, Rufan Chen, and Cheng Wang
4.1 Introduction 165
4.2 Synthesis of Organic Molecular Cages 166
4.2.1 OMCs Synthesized through Imine Reaction 167
4.2.2 OMCs Synthesized through Boronic Acid Condensation 176
4.2.3 OMCs Synthesized through Alkene/Alkyne Metathesis 180
4.2.4 OMCs Synthesized through Other Reactions 185
4.3 Functionalization of Organic Molecular Cages 188
4.4 Applications of Organic Molecular Cages 194
4.4.1 Molecular Recognition 194
4.4.2 Molecular Flask 196
4.4.3 Porous Solid 197
4.4.4 Porous Liquid 200
4.5 Conclusion and Perspective 202
References 202
5 Orthogonal Dynamic Covalent and Non-covalent Reactions 207
Dan-Wei Zhang and Zhan-Ting Li
5.1 Introduction 207
5.2 Orthogonal Dynamic Covalent Chemical Reactions 208
5.2.1 Imine and Disulfide Bonds 208
5.2.2 Imine and Boronate Ester Bonds 209
5.2.3 Hydrazone and Disulfide Bonds 210
5.2.4 Disulfide and Thioester Bonds 212
5.2.5 Imine and Alkene Bonds 212
5.2.6 Disulfide and Alkene Bonds 217
5.2.7 Disulfide, Thioester, and Hydrazone Bonds 217
5.3 Dynamic Covalent Reactions and Hydrogen Bonding 220
5.3.1 Imine, Hydrazone, and Hydrogen Bonding 220
viii
Contents
5.3.2 Disulfide and Hydrogen Bonding 228
533 Alkene Metathesis and Hydrogen Bonding 233
5.4 Imine and Hydrazone, rc-Stacking, and
Donor—Acceptor Interaction 233
5.5 Disulfide, rc-Stacking, and/or Donor—Acceptor Interaction 237
5.6 Disulfide, Hydrazone, and rc-Stacking Interaction 246
5.7 Hydrazone, Boronate, and rc-Stacking Interaction 247
5.8 Concluding Remarks 247
References 249
6 Self-sorting through Dynamic Covalent Chemistry 253
Chia-Wei Hsu and Ognjen Miljanic
6.1 Definition of Self-sorting 253
6.2 Thermodynamically Controlled Self-sorting 255
6.2.1 Purely Organic Systems 255
6.2.2 Metal-Organic Systems 259
63 Kinetically Controlled Self-sorting 270
6.3.1 Self-sorting of Dynamic Libraries during Irreversible
Chemical Reactions 275
6.3.2 Self-sorting of Dynamic Libraries under Physical Stimuli 277
6.4 Conclusions and Outlook 283
References 284
7 Dynamic Covalent Chemistry for Synthetic Molecular Machines 287
Yi Liu and Ken C.-F. Leung
7.1 Introduction 287
7.2 Molecular Machines Assembled by Dynamic
Covalent Chemistry 288
7.2.1 Mechanically Interlocked Molecular Machines 289
7.2.1.1 By Imine Chemistry 289
7.2.1.2 By Disulfide Bond Formation 295
7.2.1.3 By Olefin Metathesis 298
7.2.1.4 By Iodide-catalyzed DCvC 300
7.2.2 Non-interlocked Molecular Machines 302
7.2.2.1 Imine-based Motors 302
7.2.2.2 Imine-based Switches 303
7.2.23 Hydrazone-based Switches 304
7.3 Molecular Machines Operated by DCvC 306
7.3.1 Molecular Shuttles 307
7.3.2 Molecular Walkers 309
7.4 Concluding Remarks and Outlook 316
References 317
8 Responsive Dynamic Covalent Polymers 321
Soma Mukherjee, Jessica J. Cash, and Brent S. Sumerlin
8.1 Introduction 321
8.2 Thermoresponsive Polymers 323
8.2.1 Polymers Possessing Critical Solution Temperatures 323
8.2.2 Polymers possessing Thermo-labile Chemical Linkages 326
8.2.2.1 Polymers Containing Alkoxyamine Linkages 326
8.2.2.2 Polymers Containing Diels—Alder Linkages 327
8.3 Photo-responsive Polymers 332
8.4 Mechano-responsive Polymers 333
8.5 pH- and Chemo-responsive Polymers 336
8.5.1 Polymers Containing Acyl Hydrazone Links 336
8.5.2 Polymers Containing Imine Linkages 338
8.5.3 Polymers Containing Oxime Links 340
8.5.4 Polymers Containing Disulfide Links 342
8.5.5 Glucose-responsive Polymers 343
8.6 Conclusion 349
References 349
9 Self-healing Polymers through Dynamic Covalent Chemistry 359
Keiichi Imato and Hideyuki Otsuka
9.1 Introduction 359
9.2 Reversible Condensation Reactions 364
9.2.1 Acylhydrazone Bonds 364
9.2.2 Imine Bonds 366
9.2.3 Boronate Ester Linkages 366
9.2.4 Hemiaminal Linkages 367
9.3 Reversible Addition Reactions 367
9.3.1 Diels-Alder Reaction 367
9.3.2 Urea Bonds 371
9.4 Catalyzed Exchange Reactions 371
9.4.1 Transesterification 372
9.4.2 Olefin Metathesis 373
9.4.3 Siloxane Chemistry 374
9.5 Radical Transfer and Crossover Reactions 374
9.5.1 Disulfide and Diselenide Bonds 376
9.5.2 Thiuram Disulfide Bonds 377
9.5.3 Trithiocarbonate Linkages 377
9.6 Homolytic Bond Cleavage and Re-formation 377
9.6.1 Alkoxyamine Linkages 379
9.6.2 Diarylbibenzofuranone Linkages 379
9.7 Conclusions 381
References 383
10 Emerging Applications of Dynamic Covalent Chemistry from
Macro- to Nanoscopic Length Scales 389
Joseph C Furgai, Megan Dunn, Too Wei, and Timothy F. Scott
10.1 Introduction 389
10.2 Rearrangeable Polymer Networks 389
10.2.1 Stress Relaxation and Shape Modification 390
10.2.2 Reversible Self-healing 390
X
Contents
10.2.3 Overcoming the Limitations of Dynamic Covalent Healable Materials 397
10.3 Biotechnological Applications 400
10.3.1 Kinase Inhibitors 400
10.3.2 Micelles 401
10.3.3 Targeting and Transport 405
10.3.4 Dynamic Covalent Gels: Self-healing and Drug Delivery/Transport 406
10.3.5 Nucleic Acid Probes 411
10.4 Other Applications 411
10.4.1 Organic Electronics 411
10.4.2 Gas Storage/Capture 419
10.4.3 Catalysis 421
10.4.4 Molecular Separations 422
10.4.5 Surface Science 423
10.4.6 Color-changing Materials 425
10.4.7 Food Chemistry 427
10.4.8 Fluoride-catalyzed Silsesquioxane Bond Rearrangement 428
10.5 Conclusion 429
References 429
Index 435
DYNAMIC COVALENT CHEMISTRY
PRINCIPLES, REACTIONS, AND APPLICATIONS
The first and only exhaustive review of the theory, thermodynamic fundamentals,
mechanisms, and design principles of dynamic covalent systems
Dynamic Covalent Chemistry: Principles, Reactions, and Applications presents a comprehensive review
of the theory, thermodynamic fundamentals, mechanisms, and design principles of dynamic covalent
systems. It features contributions from a team of international scientists, grouped into three main
sections covering the principles of dynamic covalent chemistry, types of dynamic covalent chemical
reactions, and the latest applications of dynamic covalent chemistry (DCvC) across an array of fields.
The past decade has seen tremendous progress in (DCvC) research and industrial applications. The
great synthetic power and reversible nature of this chemistry has enabled the development of a variety
of functional molecular systems and materials for a broad range of applications in organic synthesis,
materials development, nanotechnology, drug discovery, and biotechnology. Vet, until now, there
have been no authoritative references devoted exclusively to this powerful synthetic tool, its current
applications, and the most promising directions for future development. Dynamic Covalent Chemistry:
Principles, Reactions, and Applications fills the yawning gap in the world literature with comprehensive
coverage of:
• The energy landscape, the importance of reversibility, enthalpy vs. entropy,
and reaction kinetics
• Single-type, multi-type, and non-covalent reactions, with a focus on the advantages
and disadvantages of each reaction type
• Dynamic covalent assembly of discrete molecular architectures, responsive polymer
synthesis, and drug discovery
• Important emerging applications of dynamic covalent chemistry in nanotechnology,
including both material- and bio-oriented directions
• Real-world examples describing a wide range of industrial applications for organic
synthesis, functional materials development, nanotechnology, drug delivery and more
Dynamic Covalent Chemistry: Principles, Reactions, and Applications is must-reading for researchers
and chemists working in dynamic covalent chemistry and supramolecular chemistry. It will also be of
value to academic researchers and advanced students interested in applying the principles of (DCvC)
in organic synthesis, functional materials development, nanotechnology, drug discovery, and
chemical biology.
Edited by
WEI ZHANG, PhD, is a professor in the Department of Chemistry and Biochemistry at the University
of Colorado, Boulder, USA. He has been an active researcher of dynamic covalent chemistry for over
15 years.
YINGHUA JIN, PhD, is a Senior Research Associate, affiliated with both the Department of Chemical
and Biological Engineering and the Department of Chemistry and Biochemistry at the University of
Colorado, Boulder, USA.
Cover Design: Wiley
Cover Image: Courtesy of Wei Zhang
www.wiley.com
J I L fS Also available
▼ ▼ 1 1 - 1—i 1 ® as an e-book
ISBN 978-1-119-07563-9
|
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| spelling | Dynamic covalent chemistry principles, reactions, and applications edited by Wei Zhang (Department of Chemistry and Biochemistry, University of Colorado, USA), Yinghua Jin (Department of Chemical and Biological Engineering and Department of Chemistry and Biochemistry, University of Colorado, USA) Hoboken, NJ, USA ; Chichester, West Sussex, UK Wiley 2018 xvi, 441 Seiten Illustrationen, Diagramme (teilweise farbig) txt rdacontent n rdamedia nc rdacarrier Supramolecular chemistry Macromolecules Chemical bonds Chemistry Supramolekulare Struktur (DE-588)4208977-3 gnd rswk-swf Chemische Bindung (DE-588)4009843-6 gnd rswk-swf (DE-588)4143413-4 Aufsatzsammlung gnd-content Chemische Bindung (DE-588)4009843-6 s Supramolekulare Struktur (DE-588)4208977-3 s DE-604 Zhang, Wei edt Jin, Yinghua edt Erscheint auch als Online-Ausgabe 978-1-119-07573-8 Digitalisierung UB Bayreuth - ADAM Catalogue Enrichment application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=030077458&sequence=000003&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis Digitalisierung UB Bayreuth - ADAM Catalogue Enrichment application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=030077458&sequence=000004&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA Klappentext |
| spellingShingle | Dynamic covalent chemistry principles, reactions, and applications Supramolecular chemistry Macromolecules Chemical bonds Chemistry Supramolekulare Struktur (DE-588)4208977-3 gnd Chemische Bindung (DE-588)4009843-6 gnd |
| subject_GND | (DE-588)4208977-3 (DE-588)4009843-6 (DE-588)4143413-4 |
| title | Dynamic covalent chemistry principles, reactions, and applications |
| title_auth | Dynamic covalent chemistry principles, reactions, and applications |
| title_exact_search | Dynamic covalent chemistry principles, reactions, and applications |
| title_full | Dynamic covalent chemistry principles, reactions, and applications edited by Wei Zhang (Department of Chemistry and Biochemistry, University of Colorado, USA), Yinghua Jin (Department of Chemical and Biological Engineering and Department of Chemistry and Biochemistry, University of Colorado, USA) |
| title_fullStr | Dynamic covalent chemistry principles, reactions, and applications edited by Wei Zhang (Department of Chemistry and Biochemistry, University of Colorado, USA), Yinghua Jin (Department of Chemical and Biological Engineering and Department of Chemistry and Biochemistry, University of Colorado, USA) |
| title_full_unstemmed | Dynamic covalent chemistry principles, reactions, and applications edited by Wei Zhang (Department of Chemistry and Biochemistry, University of Colorado, USA), Yinghua Jin (Department of Chemical and Biological Engineering and Department of Chemistry and Biochemistry, University of Colorado, USA) |
| title_short | Dynamic covalent chemistry |
| title_sort | dynamic covalent chemistry principles reactions and applications |
| title_sub | principles, reactions, and applications |
| topic | Supramolecular chemistry Macromolecules Chemical bonds Chemistry Supramolekulare Struktur (DE-588)4208977-3 gnd Chemische Bindung (DE-588)4009843-6 gnd |
| topic_facet | Supramolecular chemistry Macromolecules Chemical bonds Chemistry Supramolekulare Struktur Chemische Bindung Aufsatzsammlung |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=030077458&sequence=000003&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=030077458&sequence=000004&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT zhangwei dynamiccovalentchemistryprinciplesreactionsandapplications AT jinyinghua dynamiccovalentchemistryprinciplesreactionsandapplications |