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Room‐Temperature Columnar Liquid‐Crystalline Perylene Imido‐Diesters by a Homogeneous One‐Pot Imidification–Esterification of Perylene‐3,4,9,10‐tetracarboxylic Dianhydride
Author(s) -
Kelber Julien,
Bock Harald,
Thiebaut Olivier,
Grelet Eric,
Langhals Heinz
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001346
Subject(s) - chemistry , perylene , alkyl , imide , amine gas treating , mesogen , alcohol , polymer chemistry , organic chemistry , phase (matter) , medicinal chemistry , photochemistry , molecule , liquid crystalline
Abstract 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.