Theoretical Study on Structure and Electronic Properties of 4H-Cyclopenta[2,1-b,3;4-b’]dithiopene S-oxide and Its CCl2 and CF2 Bridged Derivatives

Banjo Semire(1*), Olusegun Ayobami Odunola(2)

(1) Department of Pure and Applied Chemistry, Ladoke Akintola University of Technology, P.M.B. 4000, Ogbomoso, Oyo-State
(2) Department of Pure and Applied Chemistry, Ladoke Akintola University of Technology, P.M.B. 4000, Ogbomoso, Oyo-State
(*) Corresponding Author


Quantum chemical calculations using semi-empirical, ab initio, density functional theory (DFT) and Møller plesset (MP2) methods were performed on 4H-Cyclopenta[2,1-b,3;4-b’]dithiopene S-oxide derivatives (i.e. bridged dithiophene S-oxides, BTOs). The geometries, stabilities, electronic and thermodynamic properties of the compounds were studied. The thermodynamic parameters calculated at PM3 were in good agreement with those calculated at B3LYP/6-31G(d) level. The band gap energies calculated at B3LYP/6-31G(d) level for the BTOs were lower than the un-substituted trithiophene but higher than 4H-Cyclopenta[2,1-b,3;4-b’]dithiopene. The absorption λmax calculated using TD-DFT was shifted to longer wavelength by successive replacement of methylene hydrogens of BTO by chlorine and fluorine atoms.


electronic properties; bridged dithiophene S-oxides; quantum chemical methods

Full Text:

Full Text Pdf


[1] Amazonas, J.G., Guimarães, J.R., Costa, S.C.S., Laks, B., and Nero, J.D.J., 2006, J. Mol. Struct. THEOCHEM, 759(1-3), 87–91.

[2] Xing, Y., Xu, X., Wang, F., and Lu, P., 2006, Opt. Mater., 29(4), 407–409.

[3] Geiger, F., Stoldt, M., Schweizer, H., Bäuerle, P., and Umbach, E., 1993, Adv. Mater., 5(2), 922–925; Garnier, F., Horowitz, G., Peng, X., and Fichou, D., 1990, Adv. Mater., 2, 562–568.

[4] Gill, R.E., Malliaras, G.G., Wildeman, J., and Hadziioannou, G., 1994, Adv. Mater., 6, 132–139.

[5] Bauerle, P., “Sulfur-Containing Oligomers” in Electronic Materials: The Oligomer Approach, Mullen, K., and Wegner G., Eds., Wiley–VCH, Weinheim, NY, 1998, 105–197.

[6] Cornil, J., Beljonne, D., and Bredas, J.L., “A Quantum Chemical Approach to Conjugated Oligomers: The Case of Oligothiopenes”, in Electronic Materials: The Oligomer Approach, Mullen, K., and Wegner G., Eds., Wiley–VCH, Weinheim, NY, 1998, 432–447.

[7] Hasnaoui, K., Makayssi, A., Hamidi, M., and Bouachrine, M., 2008, J. Iran. Chem. Res., 1, 67–77.

[8] Bredas, J.L., 1985, J. Chem. Phys., 82, 3808–3816.

[9] Ferraris, J.P., and Lambert, T.L., 1991, J. Chem. Soc., Chem. Commun., 18, 1268–1270.

[10] Gunataunga, S.R., Jones, G.W., Kalaji, M., Murphy, P.J., Taylor, D.M., and Williams, G.O., 1997, Synth. Met., 84, 973–974.

[11] De Oliveira, M.A., Duarte, H.A., Pernaut, J.M., and de Almeida, W.B., 2000, J. Phys. Chem. A., 104(35), 8256–8262.

[12] De Oliveira, M.A., Dos Santos, H.F., and de Almeida, W.B., 2002, Int. J. Quantum Chem., 90(2), 603–610.

[13] Odunola O.A., and Semire, B., 2008, Asian J. Chem., 20(6), 4343–4352.

[14] Bundgaard, E., and Krebs, F.C., 2006, Macromolecules, 39(8), 2823–2831.

[15] Van Duren, J.K.J., Dhanabalan, A., van Hal, P.A., and Janssen, R.A.J., 2001, Synth. Met., 121(1-3), 1587–1588.

[16] Yoshino, K., Park, D.H., Park B.K., Onoda, M., and Sugimoto, R., 1998, Solid State Commun., 67(12), 1119–1121.

[17] Petersen, M.H., Hagemann, O., Nielsen, K.T., Jørgensen, M., and Krebs, F.C., 2007, Sol. Energy Mater. Sol. Cells, 91, 996–1009.

[18] Ashraf, R.S., and Klemm, E.J., 2006, J. Polym. Sci., Part A: Polym. Chem., 43(24), 6445–6454.

[19] Bouzzine, S.M., Bouzakraoui, S., Bouachrine, M., and Hamidi. M., 2005, J. Mol. Struct. THEOCHEM, 726, 271–276.

[20] Bouzzine, S.M. Hamidi, M., and Bouachrine, M., 2009, Orbital, 1(2), 203–210.

[21] Aouchiche, H.A., Djennane, S., and Boucekkine, A., 2004, Synth. Met., 140(2-3), 127–134.

[22] Semire, B., Odunola, O.A., and Adejoro, I.A., 2012, J. Mol. Model., 18(6), 2755–2760.

[23] Shirakawa, H., Louis, E.J., Macdiarmid, .A.G., Chang, C.K., and Heeger A.J., 1977, J. Chem. Soc. D, 16, 578–580.

[24] Springborg M., 2003, Synth. Met., 135, 347–353.

[25] Bakhshi, A.K., Yamagudi, Y., Ago, H., and Yamabe, T., 1998, J. Mol. Struct. THEOCHEM, 437, 211–229.

[26] Inagi, S., Hosaka, K., Hayashi, S., and Funchigami, T., 2010, J. Electrochem. Soc., 157 (5), E88–E91.

[27] Becke, A.D., 1993, J. Chem. Phys., 98(7), 5648–5652.

[28] Lee, C., Yang, W., and Parr, R.G., 1988, Phys. Rev. B: Condens. Mater., 37(2), 785–789.

[29] Brasca, R., Kneeteman, M.N., and Mancini, P.M.E., 2007, IDECEFYN, 12, 54–57.

[30] Armelin, E., Bertran, O., Estrany, F., Salvatella, R., and Alemán, C., 2009, Eur. Polym. J., 45(8), 2211–2221.

[31] De Olivera, M.A., De Almeida, W.B., and Dos Santon, H.F., 2004, J. Braz. Chem. Soc., 15(6), 832–838.

[32] Kim, K-D., Park, J-S., Kim, H-K., Lee, T-B., and No, K-T., 1998, Macromolecules, 31(21), 7267–7272.

[33] Coppo, P., and Turner, M.L., 2005, J. Mater. Chem., 15, 1123–1133.

[34] Silverstein M., Basseler, G.C., and Morill, C., Spectrometric Identification of Organic compounds, Wiley, New York, 1981.

[35] Liu, G., and Yu, J., 2005, J. Mol. Struct. THEOCHEM, 717(1-3), 15–19.

[36] Semire, B., Oyebamiji, B., and Ahmad, M., 2012, Pak. J. Chem., 2(4), 166–173.

[37] Oliva M.M., Gonzalez, S.R., Casado, J., Lopez Navarrete, J.T., Seixasde Melo, J.S., and Rojen, S., 2009, Port. Electrochim. Acta, 27(5), 531–537.

[38] Casado, J., Hernández, V., Kim, O-K., Lehn, J-M., Navarrete, J.T.L., Ledesma, S.D., Ortiz, R.P., Delgado, M.C.R., Vida, Y., and Pérez-Inestrosa, E., 2004, Chem. Eur. J., 10(6), 3805–3816.

[39] Casado ,J., Hernández, V., Delgado, M.C.R, Ortiz, R.P., Navarrete, J.T.L., Facchetti, A., and Marks, T.J., 2005, J. Am. Chem. Soc., 127(38), 13364–13372.


Article Metrics

Abstract views : 1389 | views : 1332

Copyright (c) 2015 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.


Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Analytics View The Statistics of Indones. J. Chem.