Room-temperature columnar liquid-crystalline perylene imido-diesters by a homogeneous one-pot imidification-esterification of perylene-3,4,9,10- tetracarboxylic dianhydride

摘要

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-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. Perylenetetracarboxylic monoimide-diesters were synthesized by an amine-efficient, one-pot procedure. Alkyl group exchange of the ester moieties leads, through the use of the monoimido-monoanhydride, to room-temperature hexagonal columnar liquid crystals with potential as self-assembling electron acceptors for organic electronics.