ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis and characterization of oligo-4-[(pyridin-3-ylimino)methyl]phenol

İ. Kaya, S. Çulhaoğlu, and D. Şenol

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

E-mail: kayaismet@hotmail.com

Received: 1 September 2006  Revised: 25 November 2006  Accepted: 25 November 2006

Abstract: The oxidative polycondensation of 4-[(pyridin-3-ylimino)methyl]phenol (4-PIMP) with O₂, H₂O₂, and NaOCl was studied in an aqueous alkaline medium between 50°C and 90°C. Oligo-4-[(pyridin-3-ylimino)methyl]phenol (O-4-PIMP) prepared was characterized by ¹H-NMR, ¹³C-NMR, FT-IR, UV-VIS, size-exclusion chromatography, and elemental and thermal analyses techniques. At the optimum reaction conditions, the yield of O-4-PIMP was 18.9%, 39.4%, and 46.8% using H₂O₂, O₂, and NaOCl oxidant, respectively. According to the TG analysis, the initial degradation temperature of O-4-PIMP was 218°C, which was by 50°C higher than that of 4-PIMP. Thermal analyses of 4-PIMP and O-4-PIMP were carried out in N₂ atmosphere at 15–1000°C. The highest occupied molecular orbital, the lowest unoccupied molecular orbital, and electrochemical energy gaps of 4-PIMP and O-4-PIMP were determined from the onset potentials for n-doping and p-doping, respectively. Also, optical band gaps of 4-PIMP and O-4-PIMP were determined according to UV-VIS measurements.

Keywords: oxygen - hydrogen peroxide - NaOCl - oligo-4-[(pyridin-3-ylimino)methyl]phenol - oxidative polycondensation - thermal analysis - electrical conductivity

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-007-0020-9

Chemical Papers 61 (3) 199–205 (2007)