Structure property relationship study on new cubane-1,4-dicarboxylic acid derivatives

Three new series of cubane-1,4-dicarboxylic acid derivatives have been prepared as bis[(4'-alkyl)phenyl]cubane-1,4-dicarboxylates, bis[(4'-alkoxy)phenyl]cubane-1,4-dicarboxylates, and two chiral derivatives as bis(cholestenyl)cubane-1,4-dicarboxylate and (S)- bis{4'-[(2-methylbutyl)oxycarbonyl}phenyl}cubane-1,4-dicarboxylate. These ester type compounds have the bulky cubane skeleton as a central building block in their core system. The lower homologues of the alkoxyphenyl ester series exhibited nematic, the higher ones smectic A phase. The mesophase formation was supressed in case of the (4-alkyl)phenyl- and chiral derivatives.