This study examined the oxidative polycondensation reaction of 2-[(pyridin-4-yl-)methyleneamino]pyridine-3-ol (2-PMAP) using air O(2) and NaOCl oxidants at various temperatures and times in aqueous alkaline and acidic media. Under these reactions, the optimum reaction conditions using air O(2) and NaOCl oxidants were determined for 2-PMAP. The number-average molecular weight (M(n)), weight average molecular weight (M(w)), and polydispersity index (PDI) values of O-2-PMAP synthesized in aqueous alkaline media were found to be 960, 1230, and 1.281 g mol(-1), using NaOCl, and 1030, 1520, and 1.476 g mol(-1), using air O(2), respectively. At the optimum reaction conditions, the yield of O-2-PMAP in aqueous alkaline media was 92.50% and 85.70% for air O(2) and NaOCl oxidants, respectively. The yield of O-2-PMAP in aqueous acidic media was 88.5% and 88.0% for NaOCl and air O(2) oxidants, respectively. O-2-PMAP was characterized by (1)H-, (13)C-NMR, FT-IR, UV-vis, SEC, and elemental analysis. TGA-DTA analysis revealed O-2-PMAP and its oligomer metal complex compounds, such as Co(+2), Ni(+2), and Cu(+2), to be stable against thermal decomposition and their weight losses at 1000 degrees C were found to be 73.0, 58.0, 53.5%, and 50.0%, respectively. In addition, the antimicrobial activities of the monomer and oligomer were tested against E. Coli (ATCC 25922), E. Faecelis (ATCC 29212), P. Auroginasa (ATCC 27853), and S. Aureus (ATCC 25923).