Synthesis and complexation of amphiphilic calix[4]arene phosphonates with organic molecules in solutions and Langmuir-Blodgett films

A family of amphiphilic alkoxycalix[4]arenes bearing phosphonyl groups directly attached to para positions of the aromatic rings is synthesized by the Arbuzov reaction of para-bromoalkoxycalix[4]arenes with alkyl esters of phosphorus (III) acid in the presence of NiBr2. Amphiphilicity of the calixarene phosphonates is controlled by varying the quantities of the hydrophilic phosphoryl groups at the upper rim and the hydrophobic alkyl groups at the lower rim. Complexation of the calixarenes with benzene derivatives and iso-butanol in solutions is studied by RP HPLC and IR spectroscopy methods. Langmuir-Blodgett films of the calixarene phosphonates are prepared. Physical characteristics and complexation of the films with volatile organic molecules are characterized. (C) 2011 Elsevier B.V. All rights reserved.