The effects of temperature (50-80 degrees C), reaction time (up to 15 h) as well as type and concentration of oxidizing agent (NaOCl, air O-2, H2O2) on the course of oxidative Polymerization of 4-[(pyridin-2-yl-imino)methyl]phenol (4-PIMP) in aqueous alkaline medium, and on the yield of the oligomers formed (O-4-PIMP) were investigated. The optimal conditions 1 of the process have been found. Reaction products were characterized using the following methods: H-1 NMR, C-13 NMR, FT-IR, UV-VIS, gel permeation chromatography and thermal analyses TG-DTA. M-n values of O-4-PIMP are in the range 1250-4450. The oligomer shows better thermal stability than the monomer. On the basis of voltammetric measurements' results the electrochemical properties of 4-PIMP and O-4-PIMP were characterized in detail, including an effect of iodine doping of O-4-PIMP on the electric conduction. The comparison of antibacterial activity of 4-PIMP and O-4-PIMP against 8 bacterial strains has been done.