Synthesis, characterization, and optimum reaction conditions of oligo‐2‐[(pyridine‐2‐yl‐methylene) amino] phenol

Abstract

AbstractThe reaction conditions of the oxidative polycondensation of 2‐[(pyridine‐2‐yl‐methylene) amino] phenol (2‐PMAP) with air O2, H2O2, and NaOCl were studied in an aqueous alkaline medium between 60 and 90 °C. Oligo‐2‐[(pyridine‐2‐yl‐methylene) amino] phenol (O‐2‐PMAP) was characterized with 1H 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 O2 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 O2, 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 °C. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 2717–2724, 2004