Abstract: Novel bent bolaamphiphiles 14 and 15 containing of a large bent conjugated aromatic core and two polar 1,2-diol groups in both terminal positions as well as flexible internal or external lateral alky chains attached on the central of the rigid core have been synthesized via Pd-catalyzed Suzuki and Sonogasira coupling reactions as key steps.The structure of the compounds were identified by1H NMR,13C NMR and elemental analysis.The mesogenic behavior of 14 and 15 was investigated by polarizing optical microscopy(POM).UV spectral properties and fluorescence spectra of these two compounds were tested.The result showed that both compounds represented columnar phases.The orientation of the lateral alky chain had a significant impact on the mesomorphism stability.The possible model of columnar phases was set up.They can be used as a potential blue material according to the fluorescence spectra of the compound inferred.Based on the range of the UV spectrum of the compound calculated energy gap,it inferred that they can be used as an organic semiconductor material.