Further investigation of intramolecular H-bonding in benzimidazole and EDOT containing monomer

Nurioglu A. G. , Akpinar H., Kanik F. E. , Toffoli D. , TOPPARE L. K.

JOURNAL OF ELECTROANALYTICAL CHEMISTRY, vol.693, pp.23-27, 2013 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 693
  • Publication Date: 2013
  • Doi Number: 10.1016/j.jelechem.2013.01.004
  • Page Numbers: pp.23-27


Density functional theory (OFT) calculations of the relative stabilities and harmonic vibrational spectra of four different conformers of 4,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-2-phenyl-1H-benzo[d] imidazole (BlmBEd) are presented and compared with experimental IR data. BlmBEd, containing phenyl substituted benzimidazole as the acceptor and 3,4-ethylenedioxythiophene (EDOT) as the donor unit, was electrochemically polymerized in different pH media earlier. Electronic states of nitrogen in benzimidazole unit of synthesized polymeric films were analyzed via X-ray photoelectron spectroscopy. Both DFT and XPS results suggest the presence of an intramolecular H-bond between the amine of the imidazole and the oxygen of the EDOT molecules. Additionally, the quantity of the H-bond can be controlled via treatment of an acid (trifloroacetic acid) and a base (sodium hydroxide) as we stated in our previous study. (C) 2013 Elsevier B.V. All rights reserved.