The cucurbit[n]uril family

In 1981, the macrocyclic methylene-bridged glycoluril hexamer (CB[6]) was dubbed "cucurbituril" by Mock and co-workers because of its resemblance to the most prominent member of the cucurbitaceae family of plants - the pumpkin. In the intervening years, the fundamental binding properties of CB[6] - high affinity, highly selective, and constrictive binding interactions - have been delineated by the pioneering work of the research groups of Mock, Kim, and Buschmann, and has led to their applications in wastewater remediation, as artificial enzymes, and as molecular switches. More recently, the cucurbit[n]uril family has grown to include homologues (CB[5]-CB[10]), derivatives, congeners, and analogues whose sizes span and exceed the range available with the α-, β-, and γ-cyclodextrins. Their shapes, solubility, and chemical functionality may now be tailored by synthetic chemistry to play a central role in molecular recognition, self-assembly, and nanotechnology. This Review focuses on the synthesis, recognition properties, and applications of these unique macrocycles. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.