Amphiphilic calixarenes: Probing monolayer stability by selective modification of the hydrophobic-hydrophilic balance

Abstract The synthesis of calix[4]arenes permuting 1 or 4 C12 acyl chains at the upper rim and 1 or 4 methylene ethyl ester groups at the lower rim is described. The Langmuir compression isotherms of the compounds show that in the case of 1 acyl + 1 ester, there is probably orientation parallel to the air-water interface. For the other systems, orientation is orthogonal to the interface, and for the 4 +4 compound a pseudo collapse with reorientation of the hydrophilic ester groups is observed.