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Synthesis, Characterization and Antimicrobial Properties of Oligomer and Monomer/Oligomer–Metal Complexes of 2-[(Pyridine-3-yl-methylene)amino]phenol

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Abstract

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, 1H-NMR, 13C-NMR and elemental analysis. Characterization was made by thermogravimetric analysis-differential thermal analysis (TGA-DTA), size exclusion chromatography (SEC) and solubility. The 1H-NMR and 13C-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 N2 atmosphere between 15 and 1000 °C. Antibacterial and antifungal activity of the synthesized compounds was examined against selected bacteria and fungi.

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Acknowledgement

We would like to thank to Ankara University Scientific Research Projects Commission for financial support (Project No: 2005-07-05-100).

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Correspondence to İsmet Kaya.

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Kaya, İ., Emdi, D. & Saçak, M. Synthesis, Characterization and Antimicrobial Properties of Oligomer and Monomer/Oligomer–Metal Complexes of 2-[(Pyridine-3-yl-methylene)amino]phenol. J Inorg Organomet Polym 19, 286–297 (2009). https://doi.org/10.1007/s10904-009-9270-z

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