Charge-Transfer Complex of p-Aminodiphenylamine with Maleic Anhydride: Spectroscopic, Electrochemical, and Physical Properties


KARACA E., Can H., BOZKAYA U., Pekmez N. O.

CHEMPHYSCHEM, vol.17, no.13, pp.2056-2065, 2016 (Peer-Reviewed Journal) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 17 Issue: 13
  • Publication Date: 2016
  • Doi Number: 10.1002/cphc.201600161
  • Journal Name: CHEMPHYSCHEM
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.2056-2065
  • Keywords: charge-transfer complexes, maleic anhydride, NMR spectroscopy, p-aminodiphenylamine, UV/Vis spectroscopy, ALTERNATING COPOLYMERIZATION, CONJUGATED POLYMERS, ELECTRON-DONOR, BASIS-SET, SPECTRA, ACID, POLYMERIZATION, APPROXIMATION, IRRADIATION, PERFORMANCE

Abstract

A new charge-transfer complex and the amide formed by the interaction between the electron donor of the p-aminodiphenylamine and the electron acceptor of maleic anhydride are investigated by spectroscopic methods. The amidation reaction is caused by proton and charge transfer between the maleic anhydride and p-aminodiphenylamine molecules. The Benesi-Hildebrand equation is used to determine the formation constant, the molar extinction coefficient and the standard Gibbs free energy of the complex by using UV/Vis spectroscopy. To reveal the electronic and spectroscopic properties of these molecules, theoretical computations are performed on the structures of maleic anhydride, p-aminodiphenylamine and the conformers of their charge-transfer complex. The charge-transfer complex and amidation reaction mechanism are also confirmed by IR and NMR spectroscopy and HRMS. The nature of the maleic anhydride-p-aminodiphenylamine complex is characterized by cyclic voltammetry, thermogravimetric analysis, XRD and SEM. Solid microribbons of this complex show higher thermal stability than p-aminodiphenylamine.