The oxidative polycondensation reaction conditions of 4-[(2-methoxyphenylimino) methyl] phenol (2-MPIMP) were studied by using oxidants such as air and NaOCl in an aqueous alkaline medium between 50oC and 90oC. The structures of synthesized monomer and oligomer were confirmed by FTIR, UV-vis, 1H NMR, 13C NMR and elemental analysis. The characterization was afforded by TGA-DTA, size exclusion chromatography (SEC) and solubility tests. At optimum reaction conditions, the yield of oligo-4-[(2-methoxyphenylimino) methyl] phenol (O-2-MPIMP) was found to be 38.72% and 72.21% by air and NaOCl oxidants, respectively. According to the SEC analysis, the number average molecular weight (Mn), weight average molecular weight (Mw) and polydispersity index (PDI) values of O-2-MPIMP were respectively found to be 1400, 2350 g.mol-1, and 1.679 using air and 1650, 2350 g.mol-1, and 1.424 using NaOCl. TGA-DTA analyses of O-2-MPIMP were shown to be a stable compound against thermal decomposition. The weight losses of 2-MPIMP and O-2-MPIMP were found to be 57.09% and 59.11% at 1000oC, respectively. Also, electrical conductivity of the O-2-MPIMP was measured, showing that the oligomer was a semiconductor. The highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) of monomer and oligomer were determined from the onset potentials for n-doping and p-doping, respectively. Optical band gaps (Eg) of 2-MPIMP and O-2- MPIMP were calculated from UV-vis measurements