Supramolecular Hydrogen-Bonded Liquid Crystals Formed from 4-(4′-Pyridylazophenyl)-4″–Substituted Benzoates and 4-Alkoxybenzoic Acids

Abstract

Phase diagrams of the binary mixtures of the title compounds were constructed to investigate the effect of different polar substituents, on the pyridine-based derivatives, as well as the alkoxy-chain length, on the acids, on the extent and stability of the supramolecular liquid crystal phases induced by intermolecular hydrogen bonding. None of the newly prepared pyridine-based derivatives is mesomorphic, but the hydrogen-bonded complexes are. The mixtures prepared were characterized for their mesophase behavior by differential scanning calorimetry (DSC) and polarized light microscopy (PLM). Five pyridine-based derivatives (I a-e), with molecular formula X-C6H4COOC6H4-N=N-C5H4N, were prepared that differ from each other by the substituent X. The latter varies between CH3O, CH3, H, Br, and NO2. Four 4-alkoxybenzoic acids (CnH2n+1OC6H4COOH, II 10–II 18) were used; the number of carbons (n) of their alkoxy groups varies between 10, 12, 14, and 18. Smectic C mesophase is induced in most of the binary mixtures investigated.