Induction of smectic layering in nematic liquid crystals using immiscible components IV. The effect of bulky lateral carboxyl substituents on the thermotropic behaviour of 2,5-bis[4-(n-perfluoroheptyloctyloxy)benzoyloxy]toluene

Abstract

Bulky lateral carboxylate substituents were introduced at the benzylic position of 2,5-bis[4-(n-perfluoroheptyloctyloxy)benzoyloxy]toluene by esterification of the corresponding benzyl bromide with potassium carboxylates. In spite of the bulky lateral substituents, none of the 2,5-bis[4-(n-perfluoroheptyloctyloxy)benzoyloxy]benzyl carboxylates exhibit a nematic mesophase in addition to, or instead of, the smectic mesophases. All of the crystalline and SmC-SmA transition temperatures and, with the exception of the 9-anthracene carboxylate derivative, all of the isotropization temperatures of the resulting 2,5-bis[4-(n-perfluoroheptyloctyloxy)benzoyloxy]benzyl carboxylates are lower than those of the parent toluene compound. The SmC-SmA transition decreases the most, thereby stabilizing the SmA mesophase. In most cases, the SmC mesophase is destabilized from an enantiotropic to a monotropic mesophase. There is no correlation between any of the transition temperatures and the size of the lateral substituent.