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Supramolecular liquid crystals containing isoquinoline hydrogen-bonded acceptors
Abstract:6-Dodecyloxyisoquinoline IS ( 1 ) has been synthesized and utilized as a proton acceptor to generate a series of novel mesogenic supramolecules. Two mesogenic supramolecular dimers IS-OBA and IS-COOBA have been constructed from a 1:1 molar ratio of IS complexed either with 4-decyloxybenzoic acid OBA ( 2 ) or with 4-decyloxycarbonylbenzoic acid COOBA ( 3 ). A kinked mesogenic supramolecular trimer, i.e. a double H-bonded complex (IS)-THDA, has been constructed from a 2:1 molar ratio of IS complexed with 2,5-thiophenedicarboxylic acid THDA ( 4 ). The mesogenic properties of the H-bonded complex (IS2)-THDA are compared with those of previously reported H-bonded complexes (C12PS)-THDA and (C12PP2)-THDA consisting of a 2:1 molar ratio of trans -4-dodecyloxy-4-stilbazole C12PS 2 ( 5 ) or 4-dodecyloxypyridine C12PP2 (6 ) with THDA. Significantly, the first isoquinoline-based supramolecular liquid crystals have been built, and their mesogenic properties have been introduced or modified by fused- N -heterocyclic rings.
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