Enzymatic oxidative polymerization of a new para-imine functionalized phenol derivative, 4-(4-hydroxybenzylideneamino)benzoic acid (HBBA), using horseradish peroxidase enzyme and hydrogen peroxide oxidizer has been investigated in an equivolume mixture of an organic solvent (acetone, methanol, ethanol, dimethylformamide, 1,4-dioxane, and tetrahydrofuran) and phosphate buffer (pH=5.0, 6.0, 6.8, 7.0, 7.2, 8.0, and 9.0) at different temperatures under air for 24h. The resulting oligomer, oligo(4-(4-hydroxybenzylideneamino)benzoic acid) [oligo(HBBA)], was characterized using ultraviolet-visible, Fourier transform infrared (FT-IR), H-1 nuclear magnetic resonance (NMR), cyclic voltammetry, size exclusion chromatography, differential scanning calorimetry, and thermogravimetric analyses. Polymerization involved carbon dioxide and hydrogen elimination from the monomer, and terminal units of the oligomer structure consisted of phenolic hydroxyl (-OH) groups at the ends. The polymer is mainly composed of a mixture of phenylene and oxyphenylene units according to H-1 NMR and FT-IR analyses. Effects of solvent system, temperature and buffer pH on the polymerization have been investigated in respect to the yield and molecular weight (M-n) of the product. The best condition in terms of the highest molecular weight (M-n=3000g/mol, DP similar to 15) was achieved in an equivolume mixture of 1,4-dioxane/pH 5.0 phosphate buffer condition at 35 degrees C. Electrochemical characterization of oligo(HBBA) was investigated at different scan rates. The resulting oligomer has also shown relatively high thermal stability according to thermogravimetric analysis. Copyright (c) 2015 John Wiley & Sons, Ltd.