New polycatenar Schiff bases derived from 1,3,4-thiadiazole: synthesis, mesomorphism and luminescence behaviour

Abstract

Two new series of columnar liquid crystal materials based on tetra- and hexacatenar Schiff bases were synthesised by reaction of 4-aminophenyl-1,3,4-thiadiazole derivatives with terephthalaldehyde (series 2a–f) and with 2,5-thiophenedicarbaldehyde (series 3a–f). The mesomorphic properties of these compounds were studied by differential scanning calorimetry (DSC), polarised optical microscopy (POM) and X-ray diffraction (XRD). The mesomorphic behaviour was found to be dependent on the nature of the central ring (benzene in series 2a–f, thiophene in series 3a–f), on length and on number of alkoxy chains. Both tetra- and hexacatenar compounds in series 2a–f display an enantiotropic hexagonal columnar phase. Whereas, in the case of the series 3, only the tetracatenar Schiff bases (3a, 3c and 3e) display enantiotropic hexagonal columnar mesomorphism, hexacatenar Schiff bases (3b, 3d and 3f) do not show mesomorphic properties. Photophysical studies were realised in solution and in solid state. Also, a thermogravimetric analysis was performed. A fibre obtained from compound 3b was analysed by POM showing that the mesophase is maintained in the fibre.