Three novel series of triphenylene-based derivatives possessing functional group (ester, carboxylic acid, or hydroxy) at the ends of two aliphatic chains on the opposite position of triphenylene core have been synthesized and studied on mesomorphic properties. Their chemical structures were characterized by FT-IR, H-1-NMR, C-13-NMR, MS, and the thermotropic liquid crystalline properties were also investigated by polarizing optical microscopy, differential scanning calorimetry, and X-ray diffraction. It is found that the triphenylene derivatives containing terminal carboxylic acid or hydroxyl chains in the series of 9 or 10 show themortropic columnar mesophase, while the corresponding derivatives possessing terminal esters don't show any mesomorphism.