Macrocycles

The aim of Macrocycles:Construction, Chemistry and

Nanotechnology Applications isto present a general overview of

the synthesis and structure of abroad range of macrocyclic hosts, as

well as offer commentary on theirestablished and potential uses in nano-

technological applications. The main body coversthe following classes of macromolecules:cyclophanes, crown ethers and cryptands,calixarenes, cyclodextrins, cyclotriveratylenesand cryptophanes, cucurbiturils, rotaxanes, andcatenanes. The final chapter describes thepotential utility of these compounds to functionas molecular machines and motors.

Each chapter begins by presenting a briefhistory of the compounds followed by a fairlyclear and easy-to-read account of their synthesis,and how further elaboration of the core structurescan provide more complex host molecules. Thesubject of synthesis is usually followed by a briefaccount of their molecular recognition and encap-sulation properties, often drawing upon relevantand up-to-date examples from the literature.Unfortunately, binding constants are generallyomitted from the text and essential experimentaldetails such as the complexation medium used arenot mentioned—resulting in a lack of context.

Although the text is easy to read, each chapteris presented in a rather formulaic style; alternativesynthetic procedures and binding properties fordifferent molecules are listed in a predictablecatalogue-like format. However, the use of lan-guage is sometimes clumsy and repetitive. Forexample, the phrase “What is interesting aboutthese compounds is that they are” is repeatednumerous times in the text.

The major issue with this work is the nature andstyle of the figures and illustrations. The structureslack consistency in size and style and often contain

unacceptable distortions in bond lengths and angles(e.g. p. 289, Fig. 7.33a). Certain figures are incor-rectly drawn, e.g., Fig. 3.28 purports to show theclinical agent Prohance, but is drawn as [Gd.TETA]that is not sufficiently stable to be safely used as acontrast agent. Furthermore, attempts to provideinsight into the three-dimensional (3D) conforma-tion of structures are limited and often confusing(e.g. p. 468, Figure 9.75; p. 442, Figure 9.52b). Thislimitation becomes more pronounced when host–guest conformations are discussed, as the reader isunable to gain a significant understanding of thebinding between host and guest. For example inChapter 9, 3D structures are used intermittently toillustrate how rotaxane formation occurs. In mostcases, 2D depictions of macrocycle and axis aregiven separately, leaving the reader to work outhow the components are effectively assembled.

The authors strive to reach a broad readership,including “undergraduate and postgraduate stu-dents, and researchers in other fields”. The simplewriting style is well-suited to undergraduate stu-dents and the introductory topic on small ringsystems provides enough background informationto allow an understanding of more complex systemsin later chapters. However, I would hesitate torecommend this book to undergraduate students asthe low-quality figures accompanying the text mayconfuse rather than inform beginners. Newcomersseeking a brief overview to the expanding field ofmacrocyclic chemistry will benefit from the largenumber of references, of which a significant pro-portion are from the year 2000 onwards. Insummary, this book serves as a fairly useful generalaccount of the major classes of traditional macro-cyclic hosts, but lacks the polish and criticalcommentary that this field of research needs.

David Parker, Stephen J. ButlerDepartment of ChemistryDurham University (UK)

DOI: 10.1002/anie.201105634

MacrocyclesConstruction, Chemistry andNanotechnology Applica-tions. By Frank Davis andS�amus Higson. John Wiley& Sons, Hoboken 2011.608 pp., softcover,E 57.90.—ISBN 978-0470714638

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