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Macrocycles: Construction, Chemistry and Nanotechnology Applications




Macrocycles: Construction, Chemistry and Nanotechnology Applications

Frank Davis, Séamus Higson

ISBN: 978-0-470-71463-8 March 2011 610 Pages


Macrocyclic molecules contain rings made up of seven or more atoms. They are interesting because they provide building blocks for synthesizing precise two or three dimensional structures – an important goal in nanotechnology. For example, they can be used to develop nanosized reaction vessels, cages, switches and shuttles, and have potential as components in molecular computers. They also have applications as catalysts and sensors.

Macrocycles: Construction, Chemistry and Nanotechnology Applications is an essential introduction this important class of molecules and describes how to synthesise them, their chemistry, how they can be used as nanotechnology building blocks, and their applications. A wide range of structures synthesised over the past few decades are covered, from the simpler cyclophanes and multi-ring aromatic structures to vases, bowls, cages and more complex multi-ring systems and 3D architectures such as “pumpkins”, interlocking chains and knots. Topics covered include:

  • principles of macrocycle synthesis
  • simple ring compounds
  • multi-ring aromatic structures
  • porphyrins and phthalocanines
  • cyclophanes
  • crown ethers, cryptands and spherands
  • calixarenes, resorcinarenes, cavitands, carcerands, and heterocalixarenes
  • cyclodextrins
  • cucurbiturils
  • cyclotriveratylenes
  • rotaxanes
  • catenanes
  • complex 3D architectures, including trefoils and knots

Macrocycles: Construction, Chemistry and Nanotechnology Applications distills the essence of this important topic for undergraduate and postgraduate students, and for researchers in other fields interested in getting a general insight into this increasingly important class of molecules.


1 Introduction.

1.1 Simple Ring Compounds.

1.2 Three-Dimensional Aliphatic Carbon Structures.

1.3 Annulenes.

1.4 Multi-Ring Aromatic Structures.

1.5 Porpyrins and Phthalocanines.

1.6 Conclusions.


2 Cyclophanes.

2.1 Introduction.

2.2 Cyclophanes with One Aromatic System and Aliphatic Chain.

2.3 Cyclophanes with More than One Aromatic Ring.

2.4 Napthalenophanes and Other Aromatic Systems.

2.5 Cyclophanes Containing Heteroaromatic Systems.

2.6 Ferrocenophanes.

2.7 Conclusions.



3 Crown Ethers, Cryptands and Other Compounds.

3.1 Introduction.

3.2 Crown Ethers.

3.3 Simple Complexes with Crown Ethers.

3.4 Azacrowns, Cyclens and Cyclams.

3.5 Crowns Containing Other Heteroatoms.

3.6 Lariat and Bibracchial Crown Ethers.

3.7 Cryptands.

3.8 Spherands.

3.9 Combined and Multiple Systems.

3.10 Applications of Crown Ethers and Related Compounds.

3.11 Conclusions.



4 Calixarenes.

4.1 Introduction.

4.2 History.

4.3 Structures of Calixarenes.

4.4 Chemical Modification of Calixarenes.

4.5 Complexes with Calixarenes.

4.6 Bis and Multicalixarenes.

4.7 Oxacalixarenes, Azacalixarenes and Thiacalixarenes.

4.8 Resorcinarenes: Synthesis and Structure.

4.9 Cavitands and Carcerands.

4.10 Conclusions.



5 Heterocalixarenes and Calixnaphthalenes.

5.1 Introduction.

5.2 Calixnaphthalenes.

5.3 Tropolone-Based Macrocycles.

5.4 Calixfurans.

5.5 Calixpyrroles.

5.6 Calixindoles, Calixpyridines and Calixthiophenes.

5.7 Conclusions.



6 Cyclodextrins.

6.1 Introduction.

6.2 Complex Formation by Cyclodextrins.

6.3 Cyclodextrins of Other Sizes.

6.4 Modification Reactions of Cyclodextrins.

6.5 Selectivity of Cyclodextrins.

6.6 Multiple Cyclodextrin Systems.

6.7 Polymeric Cyclodextrins.

6.8 Cyclodextrins Combined with Other Macrocyclic Systems.

6.9 Therapeutic Uses of Cyclodextrins.

6.10 Other Uses of Cyclodextrins.

6.11 Conclusions.



7 Cyclotriveratylenes and Cryptophanes.

7.1 Introduction.

7.2 Synthesis of Cyclotriveratrylenes.

7.3 Modification of Cyclotriveratrylenes.

7.4 Synthesis of Optically Active Cyclotriveratrylenes.

7.5 Modification of the Bridging Groups.

7.6 Modification of the Aromatic Rings with Organometallic Groups.

7.7 Selective Binding Applications of Cyclotriveratrylenes.

7.8 Analogues of CTV.

7.9 Synthesis and Structure of Cryptophanes.

7.10 Modification of Cryptophanes.

7.11 Complexes with Cryptophanes.

7.12 Cryptophane–Xenon Complexes.

7.13 Other Uses of Cryptophanes.

7.14 Hemicryptophanes.

7.15 Conclusions.



8 Cucurbiturils.

8.1 Introduction.

8.2 Complexation Behaviour of Simple Cucurbiturils.

8.3 Modification of Cucurbiturils.

8.4 Uses of Cucurbiturils.

8.5 Hemicucurbiturils.

8.6 Conclusions.



9 Rotaxanes and Catenanes.

9.1 Introduction.

9.2 Rotaxanes.

9.3 Catenanes.

9.4 Conclusions.



10 Other Supramolecular Systems, Molecular Motors, Machines and Nanotechnological Applications.

10.1 Introduction.

10.2 Other Molecular Systems.

10.3 Molecular Devices, Motors and Machines.

10.4 Conclusions.




“Macrocycles : Construction, Chemistry and Nanotechnology Applications distils the essence of this important topic for undergraduate and postgraduate students, and for researchers in other fields who are interested in getting a general insight into this increasingly important class of molecules.”  (Chimie Nouvelle, 1 March 2013)

  • First advanced textbook to provide an overview of this class of molecules
  • Assumes no previous knowledge, and is structured to take the reader in a logical step-by-step approach, from basic early structures through to current state of the art
  • Directed reading is given to more specialist texts for readers who want further information in given areas
  • Each chapter commences with learning objectives and concludes with a summary to help students enrolled on taught programmes
  • Contains over 100 diagrams and structural formulae to illustrate key principles and concepts
  • A companion website will contain links to resources described in the book and a library of downloadable diagrams for teaching purposes