Two discoltic-like and self-assembly organic materials are synthesized successfully. One is discotic liquid crystal (DLC; Acid-6) monomer and the other is novel discotic liquid crystal polymer (DLC-PAM). The molecular structures of DLC monomer Acid-6 and DLC-PAM are identified by FT-MS, 1H-NMR and FT-IR DLC-PAM is a side-chain liquid crystal polymer with polyacrylamide (PAM) as main chain and grafting the DLC monomer Acid-6 onto PAM as side chain; therefore, the physical properties of DLC-PAM are not only plastic like but also have DLC function. UV-Vis absorption spectra show that absorption bands are located between 200 ~ 450 nm for both compounds, suitable to be a photo-sensitized dye. X-ray diffraction study demonstrates that DLC-PAM and Acid-6 possess hexagonal columnar structure because their reciprocal spacings follow the ratio 1:√3:√4. Self-assemble to hexagonal columnar makes better carrier mobility. Two kinds of dye-sensitized solar cell (DSSC) devices are fabricated with both materials as photosensitive dyes. Through qualitative and optical analysis, it shows that the device performance of the DLC-PAM and Acid-6 used as photo-sensitized dyes within DSSCs are relatively good and power conversion efficiency of 0.28 % and 2.2 % are achieved, respectively. This proved that both DLC and DLC polymeric compounds have potential to be used as photo-sensitized dyes.