Room-Temperature Columnar Liquid-Crystalline Perylene Imido-Diesters by a Homogeneous One-Pot Imidification-Esterification of Perylene-3,4,9,10- tetracarboxylic Dianhydride
Résumé
The 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-diestersubstituted 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 imidodiesters is used to obtain acceptor-type self-assembling dyes that form a hexagonal columnar liquid crystalline phase at room temperature.