Macrocyclic and Supramolecular Chemistry

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 Frédéric 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.

Autorentext

Dr. Reed M. Izatt, Charles E. Maw Professor of Chemistry (Emeritus), Brigham Young University, U.S.A.
Reed M. Izatt received a BS degree in Chemistry from Utah State University (1951) and a PhD degree in Chemistry from Pennsylvania State University (1954). After post-doctoral work at Mellon Institute of Industrial Research, he embarked on an academic career at Brigham Young University retiring as Charles E. Maw Professor of Chemistry (1993). He is the author or co-author of over 550 publications.
Reed has edited several books, contributed numerous chapters in books, written many journal and review articles and presented plenary, invited, and regular lectures at universities worldwide; regional, national, and international chemistry conferences; and government laboratories.
Reed has been involved in research in macrocyclic chemistry since the late 1960s. Together with James Christensen, he organized the first Symposium on Macrocyclic Chemistry in Provo, Utah in 1977. This Symposium has thrived and was one of the major precursors of the present ISMSC.

Inhalt

List of Contributors xv

Preface xviii

Acknowledgements xx

1 The IzattChristensen Award in Macrocyclic and Supramolecular Chemistry: A 25?-Year History (19912016) 1
Reed M. Izatt, Jerald S. Bradshaw, Steven R. Izatt, and Roger G. Harrison

1.1 Introduction 1

1.2 International IzattChristensen Award in Macrocyclic and Supramolecular Chemistry 2

1.3 International Symposium on Macrocyclic and Supramolecular Chemistry 4

1.4 IzattChristensen 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 HostGuest 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 hostguest chemistry of CB[n- 129

6.4 High?-affinity hostguest 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 ...