Asymmetrical triphenylene derivatives containing ester or carboxylic acids as terminal substituents were synthesized and characterized by DSC, optical microscopy and X-ray diffraction. It was found that in the ester homologues, only one compound exhibits a monotropic nematic (N-D) mesophase, while most of the carboxylic acid derivatives show a hexagonal columnar (Col(h)) mesophase. Temperature dependent infrared spectra of the carboxylic acid derivatives indicate the existence of strong hydrogen bonding interactions in the isotropic, mesomorphic and solid phases.