Calixarenes, Macrocycles with (Almost) Unlimited Possibilities

摘要

The condensation reaction between p-tert-butylphenol and formaldehyde leads in a single step to good yields of cyclic oligomers in which, depending on the reaction conditions, either four, six. or eight phenol units are joined by meth-ylene bridges. The beakerlike shape of the most stable conformation of the te-tramer has led to their being given the name "calixarenes" (calix = chalice). Resoicinol can undergo condensation in a similar manner with a variety of aldehydes to afford cyclic tetramers with the same basic structure (the resorcarenes). In both cases the reaction does not require the use of dilution techniques, so that large quantities of product can be readily obtained. In addition, the parent compounds can be modified in various ways, inparticular at the phenolic hy-droxy groups or the phenyl residues; these approaches can be used separately or in combination. Calixarenes are thus ideal starting materials for the synthesis of various types of host molecules and can also act as buildingblocks for the construction of larger molecular systems with defined structures and functions. Their potential applications range from use as highly specific ligands for analytical chemistry, sensor techniques and medical diagnostics to their use in thedecontamination of waste water and the construction of artificial enzymes and the synthesis of new materials for nonlinear optics or for ultrathin layers and sieve membranes with molecular pores.