Synthesis, characterization, thermal stability, conductivity, and band gaps of substitute oligo/polyamines or polyphenol


POLYMERS FOR ADVANCED TECHNOLOGIES, vol.21, no.5, pp.337-347, 2010 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 21 Issue: 5
  • Publication Date: 2010
  • Doi Number: 10.1002/pat.1433
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.337-347
  • Keywords: oxidative polycondensation, substitute amine and imine compounds, thermal analysis, conductivity and band gap, SALICYLALDEHYDE DERIVATIVES, ELECTROCHEMICAL PROPERTIES, METAL-COMPLEXES, HEAT STABILITY, SCHIFF BASES, POLYMERS, POLYAZINES, POLYIMINES
  • Çanakkale Onsekiz Mart University Affiliated: Yes


In this study, the oxidative polycondensation reaction conditions of 3,5-dichloroaniline (DCA), 3,4,5-trimethoxyaniline (TMA), 3,5-bis(trifluoromethyl)aniline (BTFMA), and 4-{[(3,5-dichlorophenyl)imino]methyl}phenol (DCPIMP) were studied by using NaOCl oxidant in an aqueous alkaline medium between 40 and 90 degrees C. The structures of the synthesized monomer and polymer were confirmed by FT-IR, Ultraviolet-visible (UV-vis), (1)H-NMR, and (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 yields of oligo-3,5-dichloroaniline (ODCA), poly-3,4,5-trimethoxy aniline (PTMA), oligo-3,5-bis(trifluoromethyl)aniline (OBTFMA), and poly-4-{[(3,5-dichlorophenyl)imino]methyll} phenol (PDCPIMP) were found to be 98, 48, 80, and 83% in using 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 ODCA, PTMA, and OBTFMA were found to be 2200, 3800 g mol(-1), and 1.727; 4700, 75009 mol(-1), and 1.596; and 1690, 1950g mol(-1), and 1.154, respectively. According to TG analysis, the weight losses of ODCA, PTMA, OBTFMA, and PDCPIMP were found to be 78.55, 54.18, 99.38, and 59.70% at 1000 degrees C, respectively. PTMA showed higher stability against thermal decomposition. Electrical conductivity of the polymers was measured, showing that the polymer is a typical semiconductor. The highest occupied molecular orbital (HOMO), the lowest unoccupied molecular orbital (LUMO) and electrochemical band gaps (E(g)') of ODCA, PTMA, OBTFMA, and PDCPIMP were calculated from their absorption edges of cyclic voltammograms. The optical band gaps (E(g)) values of all compounds were calculated from UV-vis measurements. Copyright (C) 2009 John Wiley & Sons, Ltd.