Synthesis, Characterization, Conductivity, Band Gap, and Kinetic of Thermal Degradation of Poly-4-[(2-Mercaptophenyl) Imino Methyl] Phenol

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Kaya İ., Baycan F., Doğan F.

JOURNAL OF APPLIED POLYMER SCIENCE, vol.112, pp.1234-1243, 2009 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 112
  • Publication Date: 2009
  • Doi Number: 10.1002/app.29640
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1234-1243
  • Çanakkale Onsekiz Mart University Affiliated: Yes


The oxidative polycondensation reaction conditions of 4-[(2-mercaptophenyl) imino methyl] phenol (2-MPIMP) were studied in an aqueous acidic medium between 40 and 90 degrees C by using oxidants such as air, H(2)O(2), and NaOCl. The structures of the synthesized monomer and polymer were confirmed by FTIR, (1)H NMR, (13)C NMR, and elemental analysis. The characterization was made by TGA-DTA, size exclusion chromatography (SEC) and solubility tests. At the optimum reaction conditions, the yield of poly-4-[(2-mercaptophenyl) imino methyl]phenol (P-2-MPIMP) was found to be 92% for NaOCl oxidant, 84% for H(2)O(2) oxidant 54% for air oxidant. According to the SEC analysis, the number-average molecular weight (M(w)), weight-average molecular weight (M(w)), and polydispersity index values of P-2-MPIMP were found to be 1700 mol(-1) 1900 g mol(-1), and 1.118, using H(2)O(2); 3100 g mol(-1), 3400 g mol(-1), and 1.097, using air; and 6750 g mol(-1), 6900 g mol(-1), and 1.022, using NaOCl, respectively. According to TG analysis, the weight losses of 2-MPIMP and P-2-MPIMP were found to be 95.93% and 76.41% at 1000 degrees C, respectively. P-2-MPIMP showed higher stability against thermal decomposition. Also, electrical conductivity of the P-2-MPIMP was measured, showing that the polymer is a typical semiconductor. The highest occupied molecular orbital, the lowest unoccupied molecular orbital, and the electrochemical energy gaps (E'(g),) of 2-MPIMP and P-2-MPIMP were found to be -6.1.3, -6.09; -2.65, -2.67; and 3.48, 3.42 eV, respectively. Kinetic Q thermodynamic parameters of these compounds investigated by MacCallum-Tanner and van Krevelen methods. The values of the apparent activation energies of thermal decomposition (E(a)), the reaction order (n), pre-exponential factor (A), the entropy change (Delta S*), enthalpy change (Delta H*), and free energy change (Delta G*) were calculated from the TGA curves of compounds. (C) 2009 Wiley Periodicals, Inc. J Appl Polym Sci 112: 1234-1243, 2009