Macrocyclic and supramolecular chemistry : how Izatt-Christensen Award winners shaped the field

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Macrocyclic and supramolecular chemistry : how Izatt-Christensen Award winners shaped the field

edited by Reed M. Izatt

John Wiley & Sons, 2016

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Includes bibliographical references and index

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内容説明

This book commemorates the 25th anniversary of the International Izatt-Christensen Award in Macrocyclic and Supramolecular Chemistry. The award, one of the most prestigious of small awards in chemistry, recognizes excellence in the developing field of macrocyclic and supramolecular chemistry Macrocyclic and Supramolecular Chemistry: How Izatt-Christensen Award Winners Shaped the Field features chapters written by the award recipients who provide unique perspectives on the spectacular growth in these expanding and vibrant fields of chemistry over the past half century, and on the role of these awardees in shaping this growth. During this time there has been an upsurge of interest in the design, synthesis and characterization of increasingly more complex macrocyclic ligands and in the application of this knowledge to understanding molecular recognition processes in host-guest chemistry in ways that were scarcely envisioned decades earlier. In October 2016, Professor Jean-Pierre Sauvage and Sir J. Fraser Stoddart (author for chapter 22 "Contractile and Extensile Molecular Systems: Towards Molecular Muscles" by Jean -Pierre Sauvage, Vincent Duplan, and Frederic Niess and 20 "Serendipity" by Paul R. McGonigal and J. Fraser Stoddart respectively) were awarded the Nobel Prize in Chemistry alongside fellow Wiley author Bernard Feringa, for the design and synthesis of molecular machines.

目次

List of Contributors xv Preface xviii Acknowledgements xx 1 The Izatt-Christensen Award in Macrocyclic and Supramolecular Chemistry: A 25 -Year History (1991-2016) 1 Reed M. Izatt, Jerald S. Bradshaw, Steven R. Izatt, and Roger G. Harrison 1.1 Introduction 1 1.2 International Izatt-Christensen Award in Macrocyclic and Supramolecular Chemistry 2 1.3 International Symposium on Macrocyclic and Supramolecular Chemistry 4 1.4 Izatt-Christensen award sponsor: IBC Advanced Technologies, Inc. 6 1.5 Summary 7 References 8 2 Supramolecular Chemistry with DNA 10 Pongphak Chidchob and Hanadi Sleiman 2.1 Introduction 10 2.2 Motifs in structural DNA nanotechnology 10 2.3 Dynamic assembly and molecular recognition with DNA 13 2.4 Supramolecular assembly with hybrid DNA materials: increasing the letters of the alphabet 14 2.5 Conclusion 33 References 34 3 Anion, Cation and Ion -Pair Recognition by Macrocyclic and Interlocked Host Systems 38 Paul D. Beer and Matthew J. Langton 3.1 Introduction 38 3.2 Electrochemical molecular recognition 38 3.3 Anion recognition and sensing by macrocyclic and interlocked hosts 44 3.4 Halogen -bonding anion recognition 55 3.5 Ion-pair recognition 59 3.6 Metal -directed self -assembly 62 3.7 Conclusions 67 3.8 Acknowledgements 67 References 67 4 Perspectives in Molecular Tectonics 73 Mir Wais Hosseini 4.1 Preamble: dreams and pathway 73 4.2 Introduction 75 4.3 From tectons to networks 75 4.4 Summary and outlook 87 4.5 Acknowledgements 88 References 88 5 Three Tales of Supramolecular Analytical Chemistry 92 Margaret K. Meadows and Eric V. Anslyn 5.1 Introduction 92 5.2 Citrate sensing 93 5.3 Rapid analysis of enantiomeric excess 101 5.4 Differential sensing 109 5.5 Conclusion 123 References 123 6 Robust Host-Guest Chemistry of Cucurbit[n-uril: Fundamentals and Applications of the Synthetic Receptor Family 127 Kimoon Kim, Dinesh Shetty, and Kyeng Min Park 6.1 Personal pathway to the discovery of cucurbit[n-uril and early day developments 127 6.2 Structures and physical properties of CB[n- 129 6.3 General host-guest chemistry of CB[n- 129 6.4 High -affinity host-guest pairs 130 6.5 Functionalized CBs 133 6.6 Applications of high -affinity CB[6- complexes 134 6.7 Applications of high -affinity CB[7- complexes 137 6.8 Conclusions 140 6.9 Acknowledgements 141 References 141 7 Molecular Recognition in Biomimetic Receptors 146 Peter C. Knipe, Sam Thompson, and Andrew D. Hamilton 7.1 Molecular recognition in biological systems 146 7.2 Model systems to investigate fundamental forces 146 7.3 Recognition of more complex systems - into the realm of peptides 149 7.4 A general approach to peptide mimicry - targeting secondary structure 152 7.5 Super -secondary structures and beyond 156 7.6 Outlook 159 References 160 8 A Lifetime Walk in the Realm of Cyclam 165 Luigi Fabbrizzi 8.1 Synthesis and development of cyclam and related macrocycles 165 8.2 Macrocyclic effects and the importance of being 14 -membered 170 8.3 Cyclam promotes the redox activity of the encircled metal ion 176 8.4 Scorpionands: cyclam derivatives with an aggressive tail, biting a chelated metal from the top 180 8.5 Azacyclams: cyclam -like macrocycles with built -in functionalization 187 8.6 Conclusion 193 8.7 Acknowledgements 195 References 196 9 Porosity in Metal-Organic Compounds 200 Alexander Schoedel and Omar M. Yaghi 9.1 Introduction 200 9.2 Werner complexes 201 9.3 Hofmann clathrates 201 9.4 Coordination polymers 204 9.5 Porosity in metal-organic frameworks 209 9.6 The discovery of MOF -5: the golden age of metal-organic frameworks 211 9.7 The Cambridge Structural Database - an essential tool for MOF chemists 214 9.8 Concluding remarks 215 9.9 Acknowledgement 215 References 215 10 Cyclodextrin -based Supramolecular Systems 220 Akira Harada 10.1 Introduction 220 10.2 Cyclodextrin -containing polymers 220 10.3 CD -organometallic complexes 222 10.4 Complex formation of cyclodextrin with polymers 223 10.5 Polymerization by CDs 225 10.6 Supramolecular polymers 228 10.7 Side -chain recognition by CDs 230 10.8 CD -based molecular machines 230 10.9 Macroscopic self -assembly through molecular recognition 233 10.10 Self -healing by molecular recognition 235 10.11 Stimuli -responsive polymers 236 10.12 Conclusion 238 References 238 11 Making the Tiniest Machines 241 David A. Leigh 11.1 Introduction 241 11.2 Property effects using molecular shuttles 245 11.3 Molecular motors and ratchet mechanisms 248 11.4 Small molecules that can "walk" along molecular tracks 254 11.5 Making molecules that make molecules 257 11.6 Outlook 257 11.7 Acknowledgements 259 References 259 12 Clipping an Angel's Wings 261 Roeland J.M. Nolte, Alan E. Rowan, and Johannes A.A.W. Elemans 12.1 Introduction 261 12.2 Molecular clips 263 12.3 Molecular capsules 278 12.4 Outlook 282 12.5 Acknowledgements 282 References 283 13 From Lanthanide Shift Reagents to Molecular Knots: The Importance of Molecular and Mental Flexibility 288 Jeremy K.M. Sanders 13.1 Introduction: 1969-76 288 13.2 Metalloporphyrins 289 13.3 Macrocycles based on cholic acid 296 13.4 Designed donor-acceptor catenanes 297 13.5 Dynamic combinatorial chemistry 298 13.6 Conclusions 304 References 305 14 Texaphyrins: Life, Death, and Attempts at Resurrection 309 Jonathan L. Sessler 14.1 Introduction 309 14.2 Early days 309 14.3 Starting Pharmacyclics, Inc. 311 14.4 Early biological studies of texaphyrins 314 14.5 Clinical studies of texaphyrins at Pharmacyclics, Inc. 316 14.6 Changes in direction at Pharmacyclics, Inc. 316 14.7 Current research efforts involving texaphyrin 317 14.8 Texaphyrin -platinum conjugates 318 14.9 Acknowledgements 321 References 321 15 Macrocyclic Coordination Chemistry of Resorcin[4-arenes and Pyrogallol[4-arenes 325 Harshita Kumari, Carol A. Deakyne, and Jerry L. Atwood 15.1 Introduction 325 15.2 History of hydrogen -bonded pyrogallol[4-arene - and resorcin[4-arene -based nanocapsules 326 15.3 Metal -seamed pyrogallol[4-arene - and resorcin[4-arene -based complexes 327 15.4 Concluding remarks 342 References 342 16 Dynamic Control of Recognition Processes in Host-Guest Systems and Polymer-Polymer Interactions 346 Seiji Shinkai 16.1 Introduction 346 16.2 Dynamic control of crown ether functions by chemical and physical signals 347 16.3 Stereochemical studies of calix[n-arene derivatives 351 16.4 Ion and molecule recognition by functionalized calix[n-arenes and their application to super Na+ -sensors and novel [60-fullerene isolation methods 351 16.5 Molecular design of novel sugar -sensing systems using boronic acid-diol macrocyclization 352 16.6 From molecular machines to allosteric effects 353 16.7 From allosteric effects to aggregation -induced emission (AIE) 354 16.8 Extension of cooperative actions to polymeric and biological systems 356 16.9 Summary 357 16.10 Acknowledgements 357 References 357 17 Cation Binders, Amphiphiles, and Membrane Active Transporters 360 George W. Gokel, Saeedeh Negin, Joseph W. Meisel, Mohit B. Patel, Michael R. Gokel, and Ryan Cantwell 17.1 Introduction 360 17.2 Conceptual development of lariat ethers for transport 361 17.3 Recognition of the ability of lariat ethers to form membranes 363 17.4 Use of lariat ethers to demonstrate cation- interactions 365 17.5 Development of synthetic cation channels based on crown ethers 367 17.6 Development of synthetic anion channels based on amphiphilic peptides 370 17.7 Membrane active amphiphiles as biologically active and applicable compounds 371 17.8 Conclusion 373 References 373 18 Supramolecular Technology 377 David N. Reinhoudt 18.1 Introduction 377 18.2 Chemical sensing 378 18.3 Membrane transport 379 18.4 Nonlinear optical materials 380 18.5 Supramolecular technology for nanofabrication 380 References 382 19 Synthesis of Macrocyclic Complexes Using Metal Ion Templates 383 Daryle H. Busch 19.1 Introduction 383 19.2 Macrocycle synthesis 384 References 386 20 Serendipity 388 Paul R. McGonigal and J. Fraser Stoddart 20.1 Serendipity in scientific discovery 388 20.2 Donor-acceptor charge transfer interactions 390 20.3 Cyclodextrins (CDs) 400 20.4 Conclusions and outlook 410 References 411 21 Evolution of ZnII-Macrocyclic Polyamines to Biological Probes and Supramolecular Assembly 415 Eiichi Kimura, Tohru Koike, and Shin Aoki 21.1 Introduction 415 21.2 Zinc enzyme models from ZnII macrocyclic polyamine complexes 415 21.3 ZnII-cyclens for selective recognition of nucleobases (thymine and uracil) and manipulation of genes 427 21.4 New supramolecular assemblies with ZnII-cyclen 434 21.5 Acknowledgements 438 References 438 22 Contractile and Extensile Molecular Systems: Towards Molecular Muscles 444 Jean -Pierre Sauvage, Vincent Duplan, and Frederic Niess 22.1 Preamble: the Izatt-Christensen award and Jean -Pierre Sauvage 444 22.2 Introduction 446 22.3 Interlocking ring compounds 447 22.4 Non -interlocking compounds 456 22.5 Conclusion 458 22.6 Acknowledgements 461 References 461 Index 465

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