1,3,4-Thiadiazole-2-carboxylate esters: new synthetic methodology for the preparation of an elusive family of self-organizing materials

Abstract

A series of alkyl 5-(4-octyloxyphenyl)-1,3,4-thiadiazole-2-carboxylates has been prepared via a novel chemoselective ring-closure of appropriate tricarbonyl precursors. This paper represents the first report of a general and reproducible synthetic methodology for the preparation of 1,3,4-thiadiazole-2-carboxylate esters. The 1,3,4-thiadiazole esters synthesized were designed to evaluate the feasibility of this new core unit for potential ferroelectric applications. The core unit was found to promote strongly the formation of tilted smectic phases (the smectic C phase in particular). The 1,3,4-thiadiazole ester was found to be a stronger promoter of the smectic C phase than its phenyl-based counterpart.