Ortho-imine functionalized oligophenol was synthesized via enzymatic polymerization of 2-((4-nitrophenylimino)methyl)phenol (NPIMP). Enzymatic polymerization was catalyzed by Horseradish peroxidase (HRP) enzyme and hydrogen peroxide (H2O2) oxidizer yielded oligophenol with imine functionality on the side-chain. Effects of various factors including reaction pH, temperature and solvent system on the polymerization were studied. Optimum polymerization with the highest yield (96 %) and number-average molecular weight (Mn = 7300 g/mol, degree of polymerization ≈ 30) was accomplished using equivolume mixture of acetone/pH 7.0 phosphate buffer medium at 35 °C in 24 h under air. Characterization of the resulting oligomer was accomplished by ultraviolet-visible spectroscopy (UV-Vis), fourier transform infrared spectroscopy (FT-IR), 1H and 13C nuclear magnetic resonance (1H and 13C NMR), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), cyclic voltammetry (CV) and gel permeation chromatography (GPC). The polymerization involved elimination of hydrogen from NPIMP, and the oligomer possessed phenolic –OH end groups. The oligomer backbone was composed of oxyphenylene and phenylene repeat units. The optical band gaps (Eg) of NPIMP and oligo(NPIMP) were measured as 3.21 and 3.39 Eg, respectively. Thermal stability of the oligo(NPIMP) was also found to be relatively high, and lost 5 % of its mass at 175 °C and lost 50 % of its mass at 600 °C.