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

A series of amphiphilic calix-[4]-arenes having four hydrophobic acyl chains (C6–C12) at the macrocyclic upper rim as well as two hydrophilic dihydroxyphosphoryloxy groups at the lower rim and analogous to the diacylphosphatidic acids lipids have been synthesised and characterised. The synthesis proceeds via regioselective 1,3 lower phosphorylation of the tetra-acyl calix-[4]-arene by diethylchlorophosphate in the presence of triethylamine. The ethyl 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.