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


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°C by using oxidants such as air, H2O2, and NaOCl. the structures of the synthesized monomer and polymer were confirmed by FTIR, 1H NMR, 13C 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 H2O2 oxidant 54% for air oxidant. According to the SEC analysis, the number-average molecular weight (Mn), weight-average molecular weight (Mw), and polydispersity index values of P-2-MPIMP were found to be 1700 g mol−1, 1900 g mol−1, and 1.118, using H2O2; 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°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 −6.13, −6.09; −2.65, −2.67; and 3.48, 3.42 eV, respectively. Kinetic and thermodynamic parameters of these compounds investigated by MacCallum-Tanner and van Krevelen methods. the values of the apparent activation energies of thermal decomposition (Ea), the reaction order (n), pre-exponential factor (A), the entropy change (ΔS*), enthalpy change (ΔH*), and free energy change (ΔG*) were calculated from the TGA curves of compounds. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009


Materials Science and Engineering

Keywords and Phrases

Poly-4-[(2-Mercaptophenyl) Imino Methyl] Phenol; Band Gap; Conductivity; Kinetic; Thermal Analysis

International Standard Serial Number (ISSN)


Document Type

Article - Journal

Document Version


File Type





© 2009 Wiley-Blackwell, All rights reserved.

Publication Date

01 May 2009