Synthesis and properties of novel amphiphilic calix-[4]-arene derivatives

A series of amphiphilic calix-[4]-arenes having four hydrophobic acyl chain s (C6 C12) at the macrocyclic upper rim as well as two hydrophilic dihydrox yphosphoryloxy groups at the lower rim and analogous to the diacylphosphati dic acids lipids have been synthesised and characterised. The synthesis pro ceeds via regioselective 1.3 lower phosphorylation of the tetra-acyl calix- [4]-arene by diethylchlorophosphate in the presence of triethylamine. The e thyl groups are removed by consecutive treatment with trimethylbromosilane and methanol. All the new amphiphilic derivatives self-assemble at the air- water interface as stable Langmuir monolayers. (C) 2001 Published by Elsevi er Science Ltd.