Synthesis of organogelling, fluoride ion-responsive, cholesteryl-based benzoxazole containing intra- and intermolecular hydrogen-bonding sites

A cholesteryl-based 2-(2'-hydroxyphenyl)benzoxazole (HPB) derivative 3 linked with an amide bond was prepared through an efficient synthetic pathway. The HPB, amide, and cholesteryl groups play important roles in constructing the supramolecular gel structure. UV-vis and fluorescence spectroscopy also showed that HPB and amide groups, which provide intra- and intermolecular hydrogen bonding, respectively, also contribute the recognition of fluoride anions. (C) 2010 Elsevier Ltd. All rights reserved.