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To develop novel nematic-phase liquid-crystal (LC) materials with practical potential in optical and photovoltaic devices, the alkyl chain and halogen atom substitution in 1,2,3-triazole-based compounds were varied, and the effects on the mesophase behaviour were investigated. The 4-(4-propylcyclohexyl)phenyl 4-(1-alkyl-5-hydro/halo-1,2,3-triazol-4-yl)benzoate series  1  was successfully synthesised through tandem aerobic oxidative halogenation and click reaction via in situ activation. Except for 5-thiophene-1,2,3-triazole compound  1c-Th  displaying no mesomorphism, the other compounds  1  form enantiotropic nematic mesophases, among which compounds 5-hydro-1,2,3-triazole  1c-H  (C10) and  1d-H  (C12) (long straight chain compounds) form two mesophases (smectic C phase and nematic phase). For 5-halo-1,2,3-triazole compounds  1c-X  (× = halide), the mesomorphic temperature range was wider than for the corresponding compound  1c-H  because of the effect of the halogen atom substituent on the triazole. Density functional theory (DFT) analysis showed that the structure-property relation for series  1c-X(H)  could be defined by using the calculated dihedral angles, dipole moment, polarisability, and molecular electrostatic potential as parameters. Notably, introducing halogen atoms at the 5-position of 1,2,3-triazole can greatly broaden the mesogenic temperature range, ascribed to the weak intermolecular forces and large dipole moment in this class of compounds.

Mesophase behaviour of 1,2,3-triazole-based nematic liquid crystals influenced by varying alkyl chains and halogen atom substitution