Room‐Temperature Columnar Liquid‐Crystalline Perylene Imido‐Diesters by a Homogeneous One‐Pot Imidification–Esterification of Perylene‐3,4,9,10‐tetracarboxylic Dianhydride

Abstract

AbstractThe reaction of PTCDA (perylene‐3,4,9,10‐tetracarboxylic dianhydride) with an alcohol, a bromoalkane, and an alkylamine in the presence of DBU in DMF yields imido‐diester‐substituted perylenes. The reaction is limited to polar alcohols such as propanol, but longer alkyl chains are efficiently introduced in a second step by alkyl group exchange by using selective acidic ester hydrolysis that leaves the imide group intact. This amine‐efficient approach to imido‐diesters is used to obtain acceptor‐type self‐assembling dyes that form a hexagonal columnar liquid crystalline phase at room temperature.