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Chirality in Supramolecular Assemblies
Causes and Consequences
F. Richard Keene (Edited by), R Keene (Author)
9781118867341, Wiley
Hardback, published 11 November 2016
432 pages
24.6 x 17.5 x 2.3 cm, 0.953 kg
Supramolecular chemistry deals with the organisation of molecules into defined assemblies using non-covalent interactions, including weaker and reversible interactions such as hydrogen bonds, and metal-ligand interactions. The aspect of stereochemistry within such chemical architectures, and in particular chirality, is of special interest as it impacts on considerations of molecular recognition, the development of functional materials, the vexed question of homochirality, nanoscale effects of interactions at interfaces, biocatalysis and enzymatic catalysis, and applications in organic synthesis. Chirality in Supramolecular Assemblies addresses many of these aspects, presenting a broad overview of this important and rapidly developing interdisciplinary field. Topics covered include: This book is a valuable reference for researchers in the molecular sciences, materials science and biological science working with chiral supramolecular systems. It provides summaries and special insights by acknowledged international experts in the various fields.
List of Contributors xi Preface xiii 1 Principles of Molecular Chirality 1 1.1 General Introduction 1 1.2 Geometrical Chirality 2 1.3 Topological Chirality 25 1.4 Conclusion 39 References 39 2 Homochirogenesis and the Emergence of Lifelike Structures 44 2.1 Introduction and Scope 44 2.2 The Racemic State: Mirror Symmetry Breaking 45 2.3 Asymmetric Oligomerization 49 2.4 Biochirality in Active Sites 58 2.5 Conclusions 61 Acknowledgements 61 References 61 3 Aspects of Crystallization and Chirality 65 3.1 Introduction 65 3.2 Crystal Space Groups 65 3.3 Fundamentals of Crystallization for a Racemic Mixture 69 3.4 More Complex Crystallization Behavior 71 3.5 Multiple Crystal Forms 74 3.6 Conglomerates Revisited 85 References 90 4 Complexity of Supramolecular Assemblies 94 4.1 Introduction 94 4.2 Generating Supramolecular Chirality through Assembly of Achiral Components 96 4.3 Enantioselective Supramolecular Assemblies 121 4.4 Conclusions and Future Outlook 134 References 134 5 Chirality in the Host]Guest Behaviour of Supramolecular Systems 142 5.1 An Introduction to Chiral Recognition and its Importance 142 5.2 Chiral Hosts for Chiral Guests 143 5.3 Conclusions: Summary and Future Directions 155 References 156 6 Chiral Influences in Functional Molecular Materials 159 6.1 Introduction 159 6.2 Functional Molecular Materials in Different States 161 6.3 Switching 168 6.4 Conducting Materials 171 6.5 Magnetic Materials 173 6.6 Sensors 177 6.7 Conclusions and Outlook 180 Acknowledgements 181 References 181 7 Chirality in Network Solids 190 7.1 Introduction 190 7.2 Chirality in Inorganic Network Solids 191 7.3 Synthesis of Chiral Coordination Polymers 192 7.4 Applications of Chiral Coordination Polymers 207 7.5 Summary and Outlook 209 References 210 8 Chiral Metallosupramolecular Polyhedra 218 8.1 Introduction 218 8.2 Basic Design Principles 219 8.3 Chiral Polyhedra from Achiral Components 221 8.4 Stereochemical Communication 231 8.5 Resolution of Racemic Metallo]Supramolecular Polyhedra 236 8.6 Chiral Polyhedra from Chiral Molecular Components 239 8.7 Conclusions and Outlook 250 References 251 9 Chirality at the Solution/Solid]State Interface 257 9.1 Self]Assembly at the Solution / Solid]State Interface 257 9.2 Chirality Expression at the Solution / Solid]State Interface 258 9.3 Chiral Induction / Amplification at the Solution / Solid]State Interface 266 9.4 Towards Applications 278 9.5 Conclusions 282 References 282 10 Nanoscale Aspects of Chiral Nucleation and Propagation 285 10.1 Introduction 285 10.2 Systems of Discussion 288 10.3 Conclusions 303 References 304 11 Chirality in Organic Hosts 307 11.1 Introduction 307 11.2 Chiral Hosts in Analytical Applications 307 11.3 Chiral Hosts in Asymmetric Reactions 313 11.4 Conclusion 337 Acknowledgements 338 References 338 12 Chirality Related to Biocatalysis and Enzymes in Organic Synthesis 343 12.1 Introduction 343 12.2 Biocatalysis 344 12.3 Biocatalytic Methodologies: Kinetic/Dynamic Kinetic Resolution and Asymmetric Transformations/Chemoselective Desymmetrizations 348 12.4 Optimization of Biocatalyst Performance 351 12.5 Protein Engineering 352 12.6 Hydrolysis/Reverse Hydrolysis 356 12.7 Redox Reactions 366 12.8 C]C and Other C]X Bond Formation 380 12.9 Future and Outlook 385 References 385 Index 407
Jean]Claude Chambron and F. Richard Keene
Pedro Cintas
Roger Bishop
Jonathan A. Kitchen and Philip A. Gale
Nicholas H. Evans and Paul D. Beer
David B. Amabilino
David R. Turner
Jack K. Clegg and John C. McMurtrie
Iris Destoop and Steven De Feyter
Edward G. Latter and Rasmita Raval
Daniel Fankhauser and Christopher J. Easton
Declan P. Gavin and Anita R. Maguire
Subject Areas: Chemistry [PN]
