Synthesis, characterization, and antimicrobial properties of oligo‐4‐[(pyridine‐3‐yl‐methylene) amino] phenol

Abstract

AbstractThe oxidative polycondensation reaction conditions of 4‐[(pyridine‐3‐yl‐methylene) amino]phenol (4‐PMAP) were studied using H2O2, atmospheric O2, and NaOCl oxidants in an aqueous alkaline medium between 30°C and 90°C. Synthesized oligo‐4‐[(pyridine‐3‐yl‐methylene) amino] phenol (O‐4‐PMAP) was characterized by 1H‐, 13C NMR, FTIR, UV–vis, size exclusion chromatography (SEC), and elemental analysis techniques. The yield of O‐4‐PMAP was found to be 32% (for H2O2 oxidant), 68% (for atmospheric O2 oxidant), and 82% (for NaOCl oxidant). According to the SEC analysis, the number–average molecular weight, weight–average molecular weight, and polydispersity index values of O‐4‐PMAP was found to be 5767, 6646 g mol−1, and 1.152, respectively, using H2O2, and 4540, 5139 g mol−1, and 1.132, respectively, using atmospheric O2, and 9037, 9235 g mol−1, and 1.022, using NaOCl, respectively. According to TG and DSC analyses, O‐4‐PMAP was more stable than 4‐PMAP against thermal decomposition. The weight loss of O‐4‐PMAP was found to be 94.80% at 1000°C. Also, antimicrobial activities of the oligomer were tested against B. cereus, L. monocytogenes, B. megaterium, B. subtilis, E. coli, Str. thermophilus, M. smegmatis, B. brevis, E. aeroginesa, P. vulgaris, M. luteus, S. aureus, and B. jeoreseens. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 102: 3327–3333, 2006