The reaction conditions of the oxidative polycondensation of 2-[(pyridine2-yl-methylene) amino] phenol (2-PMAP) with air O-2, H2O2, and NaOCl were studied in an aqueous alkaline medium between 60 and 90 degreesC. Oligo-2-[(pyridine-2-yl-methylene) amino] phenol (O-2-PMAP) was characterized with H-1 NMR, Fourier transform infrared, ultraviolet-visible, size exclusion chromatography (SEC), and elemental analysis techniques. Moreover, solubility testing of the oligomer was performed in polar and nonpolar organic solvents. With the NaOCl, H2O2, and air O-2 oxidants, the conversions of 2-PMAP into O-2-PMAP were 98, 87, and 62%, respectively, in an aqueous alkaline medium. According to SEC, the number-average molecular weight, weight-average molecular weight, and polydispersity index of O-2-PMAP were 2262 g mol(-1), 2809 g mol(-1), and 1.24 with NaOCl, 3045 g mol(-1), 3861 g mol(-1), and 1.27 with air O-2, and 1427 g mol(-1), 1648 g mol(-1), and 1.16 with air H2O2, respectively. Also, thermogravimetric analysis showed that O-2-PMAP was stable against thermooxidative decomposition. The weight loss of O-2-PMAP was 96.68% at 900 degreesC. (C) 2004 Wiley Periodicals, Inc.