Chiral Carbon-rich Macrocycles and Cyclophanes

Over the last three decades, chiral carbon-rich compounds have evolved into an interesting and useful class of materials due to the many unique properties that result from the installation of conjugated chromophores within a chiral framework. Chiral carbon-rich materials possess distinct chirooptical and electronic properties that may prove useful for a number of intriguing applications ranging from optically active liquid crystals to nonlinear optical materials. Chiral carbon-rich compounds also represent a potentially valuable scaffold for use in asymmetric reactions and catalysis. 

The chiral macrocydes and cyclophanes that have been included in this Chapter have loosely been dassified with respect to the synthetic strategy employed to provide the asymmetric, cydic product. One of the simplest and most economical methods for introdudng chirality involves the use of only achiral building blocks to 

Carbon-Rich Compounds. Edited by Michael M. Haley and Rik R. Tykwinski Copyright 2006 WILEY-VCH Verlag GmbH Co. KGaA, Weinheim ISBN 3-527-31224-2 

The following discussion is intended to provide an introduction to the latest innovations in the design and synthesis of chiral carbon-rich macrocycles while providing some historical context of their development and applications. The systems under review are limited primarily to chiral macrocycles that are conjugated or that possess highly conjugated substructures. Excluded from the discussion are, for example, porphyrins [2, 3], cyclodextrins [4] and calixarenes [5], either because they do not fit within the context of our discussion or because they have been extensively reviewed elsewhere. 

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