Schiff base polymer [P-4-HMPIMP] of 4-[(4-hydroxy-2-methylphenyl)iminomethyl]-2,6-dimethylphenol (4-HMPIMP) was synthesized via oxidative polycondensation reaction in an alkaline medium with using NaOCl, H(2)O(2) or air as oxidants. The structures of the synthesized monomer and polymer were confirmed by FT-JR. UV-Vis, NMR and elemental analysis, while their properties were characterized by TG-DTA, size exclusion chromatography (SEC) and solubility tests. The influence of the type of oxidizer on M(n), M(w) and PDI values was also studied. Conductivity measurements of the polymer was done by electrometer using four point probe technique and the electrochemical and optical band gap values of both 4-HMPIMP and P-4-HMPIMP were determined by using cyclic voltammetry and UV-Vis measurements. Conductivity and band gap values indicate that this polymer is a typical semiconductor.