Liquid crystal properties of N-alkyl(ethylpyridinium) bromides omega-substituted with a mesogenic group

A new series of ethylpyridinium salts N-substituted with a 4'-methoxybiphenyl-4-yloxyalkyl group has been synthesized and the mesomorphic properties examined. The effect of positioning the ethyl group at each of the three available positions (2; 3- or 4-) on the pyridinium ring was examined and compounds with alkyl chains containing odd numbers of carbon atoms from C5 to C11 were investigated. It was found that the longer chain (C9-C11) 2- and 4-ethylpyridinium compounds form smectic phases, whereas the corresponding 3-substituted compounds do not. X-ray diffraction studies indicated that the smectic phases were of types A, B and in one case E, with the molecules lying in a head to tail fashion in single layers with interdigitated alkyl chains. We explain the difference in mesogenic properties of the three different ring-substituted compounds in terms of packing considerations in the ionic regions of the structures. It is suggested that the 3-derivatives pack more efficiently than the 2- and 4-substituted compounds.