- Room-temperature columnar liquid-crystalline perylene imido-diesters by a homogeneous one-pot imidification-esterification of perylene-3,4,9,10- tetracarboxylic dianhydride
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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.
- Kelber, Julien,Bock, Harald,Thiebaut, Olivier,Grelet, Eric,Langhals, Heinz
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