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SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL PROPERTIES OF 4-[(4-HYDROXYBENZYLIDENE) AMINO] PHENOL AND ITS POLYMER

İsmet Kaya

Department of Chemistry, Faculty of Science and Arts, Çanakkale Onsekiz Mart University, TR-17020, Çanakkale, Turkey

Corresponding author.

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Süleyman Çulhaoğlu

Department of Chemistry, Faculty of Science and Arts, Çanakkale Onsekiz Mart University, TR-17020, Çanakkale, Turkey

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Dilek Şenol

Department of Chemistry, Faculty of Science and Arts, Çanakkale Onsekiz Mart University, TR-17020, Çanakkale, Turkey

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Abstract

The oxidative polycondensation reaction conditions of 4-[(4-hydroxybenzylidene) amino] phenol (4-HBAP) were studied with H₂O₂, air oxygen and NaOCl in an aqueous alkaline medium between 50 and 90°C. The structures of the obtained monomer and polymer were confirmed by FT-IR, UV-Vis, ¹H- and ¹³C-NMR and elemental analysis. The characterization was made by TG-DTA, size exclusion chromatography (SEC) and solubility tests. At the optimum reaction conditions, the yield of poly[4-(4-hydroxybenzylidene amino) phenol] (P-4-HBAP) was found to be 48.3% (for H₂O₂ oxidant), 80.5% (for air O₂ oxidant) and 86.4% (for NaOCl oxidant). According to the SEC analysis, the number-average molecular weight (M_n), weight-average molecular weight (M_w) and polydispersity index (PDI) values of P-4-HBAP was found to be 8950, 10970 g mol^-1 and 1.225, respectively, using H₂O₂; and 11610, 15190 g mol^-1 and 1.308 respectively, using air O₂ and 7900, 9610 g mol^-1 and 1.216, respectively, using NaOCl. According to TG-DTA analyses, P-4-HBAP was more stable than 4-HBAP against thermal decomposition. The weight loss of P-4-HBAP was found to be 49.27% at 1000°C. The highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) values calculated from electrochemical measurement. Electrochemical energy gaps (E_g′) of 4-HBAP and P-4-HBAP were found to be -5.46, -5.28; -2.26, -2.67; 3.20 and 2.61 eV, respectively. According to UV-Vis measurements, optical band gap (E_g) of 4-HBAP and P-4-HBAP were found to be 3.34 and 3.01 eV, respectively. Also, antimicrobial activities of 4-HBAP and P-4-HBAP were examined against selected some bacteria. The electrical conductivity of the polymer was measured after doping with iodine.

This work was financially supported by the TUBITAK Grants Commission for a research grant (No. TBAG-2451(104T062)).

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