Crystal engineering of two diacetylene monomers was achieved by branching two chiral groups [R = PhC*MeNH(CO)CH] exhibiting an enantiopure configuration of ,-() and an achiral ,--isomer (). The X-ray structures of and reveal the presence of supramolecular arrangements driven by intermolecular H-bonding. A significant intermolecular closer proximity in than that in is depicted, ultimately resulting in a slow thermal (days) and swift (min) photochemical polymerization of to form , whereas is unreactive.
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