Synthesis, characterization, thermal stability and electrochemical properties of poly-4-[(2-methylphenyl)iminomethyl]phenol


Kaya I. , Yildirim M.

EUROPEAN POLYMER JOURNAL, vol.43, no.1, pp.127-138, 2007 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 43 Issue: 1
  • Publication Date: 2007
  • Doi Number: 10.1016/j.eurpolymj.2006.10.014
  • Title of Journal : EUROPEAN POLYMER JOURNAL
  • Page Numbers: pp.127-138
  • Keywords: oxidative polycondensation, poly-4-[(2-methylphenyl)iminomethyl]phenol, air O-2, NaOCl, H2O2, thermal analysis, conductivity and band gap, OLIGOMER-METAL COMPLEXES, BAND-GAP, CONDUCTIVITY, POLYMERS, DEGRADATION, PHENOL, POLYAZOMETHINE, POLYMERIZATION, POLYANILINE, IMINO

Abstract

In this study, the reaction conditions of poly-4-[(2-methylphenyl)iminomethyl]phenol (P-2-MPIMP) were studied by using oxidants such as air O2, H2O2 and NaOCl in an aqueous alkaline medium between 50 and 90 °C. The structures of the synthesized monomer and polymer were confirmed by FT-IR, UV–vis, 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-[(2-methylphenyl)iminomethyl]phenol (P-2-MPIMP) was found to be 20% (for air O2 oxidant), 33% (for H2O2 oxidant), and 74% (for NaOCl oxidant). According to the SEC analysis, the number-average molecular weight (Mn), weight-average molecular weight (Mw) and polydispersity index (PDI) values of P-2-MPIMP were found to be 3300, 4100 g mol-1 and 1.242, using H2O2, and 4550, 5150 g mol-1and 1.132, using air O2 and 5300, 5850 g mol-1 and 1.104, using NaOCl, respectively. According to TG analysis, the weight losses of 4-[(2-methylphenyl)iminomethyl]phenol (2-MPIMP) and P-2-MPIMP were found to be between 75.29% and 48.17% at 1000 °C, respectively. P-2-MPIMP was shown to have a higher stability against thermal decomposition. Also, electrical conductivity of the P-2-MPIMP was measured, showing that the polymer is a typical semiconductor. Electrochemically, the highest occupied molecular orbital (HOMO), the lowest unoccupied molecular orbital (LUMO) and electrochemical energy gaps ( of 2-MPIMP and P-2-MPIMP were found to be -6.01, -6.03; -2.63, -2.82; 3.38 and 3.21 eV, respectively. According to UV–vis measurements, the optical band gap (Eg) of 2-MPIMP and P-2-MPIMP was found to be 3.40 and 2.97 eV, respectively.
In this study, the reaction conditions of poly-4-[(2-methylphenyl)iminomethyl]phenol (P-2-MPIMP) were studied by using oxidants such as air O-2, H2O2 and NaOCl in an aqueous alkaline medium between 50 and 90 degrees C. The structures of the synthesized monomer and polymer were confirmed by FT-IR, UV-vis, 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-[(2-methylphenyl)iminomethyl]phenol (P-2-MPIMP) was found to be 20% (for air O-2 oxidant), 33% (for H2O2 oxidant), and 74% (for NaOCl oxidant). According to the SEC analysis, the number-average molecular weight (Mn) weight-average molecular weight (M,) and polydispersity index (PDI) values of P-2-MPIMP were found to be 3300, 4100 g mol(-1) and 1.242, using H2O2, and 4550, 5150 g mol-land 1.132, using air 02 and 5300, 5850 g mol-1 and 1.104, using NaOCl, respectively. According to TG analysis, the weight losses of 4-[(2-methylphenyl)iminomethyl]phenol (2-MPIMP) and P-2-MPIMP were found to be between 75.29% and 48.17% at 1000 degrees C, respectively. P-2-MPIMP was shown to have a higher stability against thermal decomposition. Also, electrical conductivity of the P-2-MPIMP was measured. showing that the polymer is a typical semiconductor. Electrochemically, the highest occupied molecular orbital (HOMO), the lowest unoccupied molecular orbital (LUMO) and electrochemical energy gaps (E'(g)) of 2-MPIMP and P-2-MPIMP were found to be -6.01, -6.03; -2.63, -2.82; 3.38 and 3.21 eV, respectively. According to UV-vis measurements, the optical band gap (E-g) of 2-MPIMP and P-2-MPIMP was found to be 3.40 and 2.97 eV, respectively. (c) 2006 Elsevier Ltd. All rights reserved.