The Nature of the Mechanical Bond (eBook)

Carson J. Bruns is a Miller Research Fellow in the College of Chemistry at the University of California, Berkeley. He attended Luther College (2004-2008) where he earned degrees in chemistry, religion, and mathematics. He received a PhD in organic chemistry from Northwestern University (2008-2013), where he was a National Science Foundation (NSF) Graduate Research Fellow. Researching in the United States, Thailand, Korea, and Japan, he has co-authored more than 30 publications which have collectively been cited more than 1000 times. His research interests span all aspects of the mechanical bond, from fundamental science to applied chemical technologies. J. Fraser Stoddart is a Board of Trustees Professor of Chemistry at Northwestern University. By playing a major role in introducing the mechanical bond into molecules, he is one of the few contemporary chemists to have contributed to the opening up of an entirely new field of chemistry. He has pioneered the development of bistable mechanically interlocked molecules (MIMs) for use in molecular electronic devices and drug delivery vehicles. In 2016 he shared the Nobel Prize in Chemistry with Jean-Pierre Sauvage and Ben Feringa for the design and synthesis of molecular machines.

Foreword

Preface

Acknowledgments

About the Authors

Abbreviations, Acronyms, and Symbols

Part 1 Introducing Mechanical Bonds

1 An Introduction to the Mechanical Bond

Conspectus

Introduction

1.1 The Ubiquity of the Mechanical Bond

1.2 Representing Molecular Mechanical Bonds

1.3 Aesthetics of Mechanical Bonds

1.4 Evolution of Mechanostereochemistry

References

Part 2 Making Mechanical Bonds

2 The Fundamentals of Making Mechanical Bonds

Conspectus

Introduction

2.1 Statistical Synthesis

2.2 Directed Synthesis

2.3 Template-Directed Synthesis

2.4 Active Template Synthesis

Conclusions and Outlook

References

3 Making Mechanical Bonds Under Thermodynamic Control

Conspectus

Introduction

3.1 Slippage

3.2 Self-Assembling Metallo-Organic MIMs

3.3 Mechanical Bond Formation by Condensation

3.4 Mechanical Bond Formation by Olefin Metathesis

3.5 Mechanical Bond Formation by Reversible Nucleophilic Reactions

3.6 Surface-Mounted MIMs

Conclusions and Outlook

References

Part 3 Cultivating Mechanical Bonds

4 Molecular Topologies and Architectures with Mechanical Bonds

Conspectus

Introduction

4.1 Catenane Topologies

4.2 Rotaxane Architectures

4.3 Other Architectures with Mechanical Bonds

Conclusions and Outlook

References

5 The Stereochemistry of the Mechanical Bond

Conspectus

Introduction

5.1 Dynamic Mechanostereoisomerism

5.2 Static Mechanostereoisomerism

Concluding Remarks

References

6 Molecular Switches and Machines with Mechanical Bonds

Conspectus

Introduction

6.1 Redox-Driven Switches

6.2 Photo-Driven Switches

6.3 Acid/Base-Driven Switches

6.4 Cation-Triggered Switches

6.5 Anion-Triggered Switches

6.6 Switches Driven by Molecular Recognition

6.7 Switches Driven by Covalent Reactions

6.8 Solvent-Driven Switches

6.9 Thermally Driven Switches

6.10 Pressure-Driven Switches

6.11 Switches Driven by Electric Fields

6.12 Switches Driven by Mechanical Force

6.13 Beyond Translation and Circumrotation

6.14 Condensed-Phase Switching

6.15 Mechanomolecular Motors and Machines

Conclusions and Outlook

References

Appendix A: Glossary of Terminology

Appendix B: Cover Art Gallery

Index

"This book will serve very well to inform any chemist or chemistry student curious as to the workings of molecular topology and the molecular machines that depend upon it, and should be read by anyone seeking to enter these fields. The writing is elegant and at times playful-thoroughly enjoyable to read. This book will certainly occupy pride of place in my research group' library."
Angewandte Chemie International Edition, 8th December 2016

"The book contains numerous schemes and illustrations of high quality. These facilitate the visualization of the molecular structures and of the chemical and dynamical processes. Each chapter contains approximately 500 to 1500 references and the book presents a total of 3400 unique references which corresponds to the main publications in this research domain. Undoubtedly, the book will be a most useful tool for all researchers interested in mechanically interlocked molecules ... One can anticipate, I believe, that The Nature of the Mechanical Bond will open new horizons for generations of readers and will stimulate the creativity of many architects of matter who wish to design more and more fascinating molecular systems."
Acta Cryst, November 2017

"... a spectacular book! Many chemists will want to have it on their desks and regard it as the holy writ."
--Josef Michl

"The story is told by THE inventor-pioneer-master in the field and is accompanied by amazing illustrations... [it] will become an absolute reference and a best seller in chemistry!"
--Alberto Credi

"... the great opus on the mechanical bond. A most impressive undertaking!"
--Jean-Marie Lehn

"I love the first chapter, and its romp through the mechanical bond."
--Roald Hoffman

"... what a wonderful read.... I thoroughly enjoyed the scientifically atypical perspective. A real pleasure."
--Bruce Gibb

"... comprehensive coverage [and] exceptional top-quality graphics... this [is a] definitive book."
--Paul Beer