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The Nature of the Mechanical Bond

From Molecules to Machines

Bruns, Carson J. / Stoddart, J. Fraser


1. Edition December 2016
786 Pages, Hardcover
Wiley & Sons Ltd

ISBN: 978-1-119-04400-0
John Wiley & Sons

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"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

Congratulations to co-author J. Fraser Stoddart, a 2016 Nobel Laureate in Chemistry.
In molecules, the mechanical bond is not shared between atoms--it is a bond that arises when molecular entities become entangled in space. Just as supermolecules are held together by supramolecular interactions, mechanomolecules, such as catenanes and rotaxanes, are maintained by mechanical bonds. This emergent bond endows mechanomolecules with a whole suite of novel properties relating to both form and function. They hold unlimited promise for countless applications, ranging from their presence in molecular devices and electronics to their involvement in remarkably advanced functional materials. The Nature of the Mechanical Bond is a comprehensive review of much of the contemporary literature on the mechanical bond, accessible to newcomers and veterans alike. Topics covered include:
* Supramolecular, covalent, and statistical approaches to the formation of entanglements that underpin mechanical bonds in molecules and macromolecules
* Kinetically and thermodynamically controlled strategies for synthesizing mechanomolecules
* Chemical topology, molecular architectures, polymers, crystals, and materials with mechanical bonds
* The stereochemistry of the mechanical bond (mechanostereochemistry), including the novel types of dynamic and static isomerism and chirality that emerge in mechanomolecules
* Artificial molecular switches and machines based on the large-amplitude translational and rotational motions expressed by suitably designed catenanes and rotaxanes.
This contemporary and highly interdisciplinary field is summarized in a visually appealing, image-driven format, with more than 800 illustrations covering both fundamental and applied research. The Nature of the Mechanical Bond is a must-read for everyone, from students to experienced researchers, with an interest in chemistry's latest and most non-canonical bond.

Read the Preface




About the Authors

Abbreviations, Acronyms, and Symbols

Part 1 Introducing Mechanical Bonds

1 An Introduction to the Mechanical Bond



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


Part 2 Making Mechanical Bonds

2 The Fundamentals of Making Mechanical Bonds



2.1 Statistical Synthesis

2.2 Directed Synthesis

2.3 Template-Directed Synthesis

2.4 Active Template Synthesis

Conclusions and Outlook


3 Making Mechanical Bonds Under Thermodynamic Control



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


Part 3 Cultivating Mechanical Bonds

4 Molecular Topologies and Architectures with Mechanical Bonds



4.1 Catenane Topologies

4.2 Rotaxane Architectures

4.3 Other Architectures with Mechanical Bonds

Conclusions and Outlook


5 The Stereochemistry of the Mechanical Bond



5.1 Dynamic Mechanostereoisomerism

5.2 Static Mechanostereoisomerism

Concluding Remarks


6 Molecular Switches and Machines with Mechanical Bonds



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


Appendix A: Glossary of Terminology

Appendix B: Cover Art Gallery

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

"... 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
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.

J. F. Stoddart, Northwestern University, USA