Hydrogen-bonded liquid crystals formed from 4-alkoxystilbazoles and chlorophenols

Hydrogen-bonded complexes are formed between two chain lengths of 4-alkoxystilbazoles and six different chlorophenols. Single crystal structure determinations were possible for four of the complexes, all of which showed a similar dimeric motif in which two chlorophenols formed a loose back-to-back dimer with a stilbazole hydrogen-bonded at either side. Two of the complexes showed similarities in their three-dimensional packing. Liquid crystal properties were found for all complexes except those containing pentachlorophenol. The phase behaviour of the longer-chain dodecyloxystilbazole complexes was dominated by the observation of the smectic A phase, while both nematic and smectic A phases were found for the octyloxy homologues. The mesophase stability was appreciably lower in these new complexes when compared with fluorophenol analogues reported previously, attributed to a reduction in anisotropy on account of the effects of the greater size of chlorine compared with fluorine.