Oligo-2-[(pyridine-3-yl-methylene)amino]phenol (2-PMAP) is synthesized by the oxidative polycondensation (OP) in aqueous alkaline medium using air as oxidant. At optimum reaction conditions, the yield of products is 71%. The structures of the monomer and oligomer were confirmed by FT-IR, UV-Vis, H-1-NMR, C-13-NMR and elemental analysis. Characterization was made by thermogravimetric analysis-differential thermal analysis (TGA-DTA), size exclusion chromatography (SEC) and solubility. The H-1-NMR and C-13-NMR data show that polymerization proceeds by C-C and C-O coupling of the ortho and para positions (-OH group and oxyphenylene group) of 2-[(pyridine-3-yl-methylene)amino]phenol. The molecular weight distribution of the product was determined by SEC. The number-average molecular weight (M (n) ), weight-average molecular weight (M (w) ) and polydispersity index (PDI) of O-2-PMAP are 7150, 8000 g mol(-1) and 1.119 for air oxidant, respectively. Thermal analysis results of O-2-PMAP indicate stability against thermal decomposition. Thermal analyses of 2-PMAP, 2-PMAP-Cd, 2-PMAP-Co, 2-PMAP-Cu, 2-PMAP-Zn, O-2-PMAP, O-2-PMAP-Cd, O-2-PMAP-Co, O-2-PMAP-Cu and O-2-PMAP-Zn monomer/oligomer-metal complexes were investigated under a N-2 atmosphere between 15 and 1000 A degrees C. Antibacterial and antifungal activity of the synthesized compounds was examined against selected bacteria and fungi.