Effect of side chain length on the stability and structural properties of 3-(2’,5’-dialkoxyphenyl)thiophenes: a theoretical study

  • Taye Beyene Demissie Department of Chemistry, Hawassa University, P.O. Box 05, Hawassa, Ethiopia
  • Shimelis Admassie Department of Chemistry, Addis Ababa University, P.O. Box, 1176, Addis Ababa, Ethiopia
  • Ahmed M. Mohammed Department of Chemistry, Addis Ababa University, P.O. Box, 1176, Addis Ababa, Ethiopia
  • Wendimagegn Mammo Department of Chemistry, Addis Ababa University, P.O. Box, 1176, Addis Ababa, Ethiopia
Keywords: Density functional theory, Hartree-Fock, Dialkoxyphenylthiophenes

Abstract

We report on the effect of the alkoxy chain length on the thermodynamic properties of neutral and the corresponding radical cations of 3-(2’,5’-dibutyloxyphenyl)thiophene (DBOPT), 3-(2’,5’-diheptyloxyphenyl)thiophene (DHOPT), and 3-(2’,5’-dioctyloxyphenyl)thiophene (DOOPT) and their dimers studied by Hartree-Fock (HF) and Density Functional Theory (DFT) methods. The DFT calculations suggest that dimers of the dialkoxyphenylthiophenes with longer side chains are thermodynamically more stable by about 61.39 kJ/mol than the ones with shorter side chains at the radical cation state. The results correlate well with the experimental observations made during the electrochemical synthesis of these polymers from their monomers.

KEY WORDS: Density functional theory, Hartree-Fock, Dialkoxyphenylthiophenes

Bull. Chem. Soc. Ethiop. 2010, 24(1), 93-102.

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eISSN: 1726-801X
print ISSN: 1011-3924