Oxidative polycondensation of 3-(1-(2-phenylhydrazono)ethyl)phenol (3-PHEP) was studied using oxidants such as sodium hypochlorite, air (O2) and hydrogen peroxide in an aqueous alkaline medium under various polymerization conditions. The polymerization yield, molecular weight, solubility, and thermostability of the polymer were investigated. The macromolecular structure of the resulting polymer was characterized by elemental analysis, ultravioletvisible, Fourier transform infrared, and nuclear magnetic resonance techniques. Thermogravimetric analysis showed poly(3-PHEP) to be highly stable against thermo-oxidative decomposition. Mass loss of the polymer was found to be only 16.3% at 1000 degrees C. In addition, the highest occupied molecular orbitallowest unoccupied molecular orbital energy levels, electrochemical (Eg') band gaps and optical (Eg) band gaps were calculated from cyclic voltammetry and ultravioletvisible measurements, respectively. (c) 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013