Synthesis and thermotropic properties of new polyacrylates containing alkanoyl-substituted azobenzene mesogens

The synthesis and characterization of a series of new polyacrylates 1, containing the azobenzene mesogen spaced from the backbone by a hexamethylene segment and substituted in the 4-position by an alkanoyl chain of variable length, together with those of the relevant precursors are reported. Optical and X-ray analyses provided evidence for the presence of a smectic A mesophase in a fairly broad range of temperature in both polymers and low molar mass compounds. In polyacrylates 1, the side-chain substituents were fully interdigitated in a smectic A 1 structure. The comparison of the transition parameters of polymers 1 with those of another series of polyacrylates 7 containing the azobenzene unit substituted in the 4-position by an alkyloxy chain of variable length revealed that the replacement of an oxygen atom by a carbonyl group strongly enhanced the smectogenic character of the azobenzene group.