Do [all]-S,S'-Dioxide Oligothiophenes Show Electronic and Optical Properties of Oligoenes and/or of Oligothiophenes?

A comprehensive photophysical and spectroscopic (electronic and Raman) study guided by density functional theory, DFT, CIS, and correlated ab initio calculations has been performed on a series of fully oxidized oligothiophenes with variable chain length, and up to four rings. A comparison with the p...

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Publicado en:Journal of the American Chemical Society Vol. 132; no. 17; pp. 6231 - 6243
Autores principales: Oliva, María Moreno, Casado, Juan, López Navarrete, Juan T., Patchkovskii, Serguei, Goodson III, Theodore, Harpham, Michael R., Seixas de Melo, J. Sérgio, Amir, Elizabeta, Rozen, Shlomo
Formato: Artículo
Publicado: American Chemical Society 5/5/2010
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Acceso en línea:Ver este registro en EBSCOhost
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      pub: American Chemical Society
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        50730878
        10.1021/ja101015q
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        atl: Do [all]-S,S'-Dioxide Oligothiophenes Show Electronic and Optical Properties of Oligoenes and/or of Oligothiophenes?
      aug:
        au:
          Oliva, María Moreno
          Casado, Juan
          López Navarrete, Juan T.
          Patchkovskii, Serguei
          Goodson III, Theodore
          Harpham, Michael R.
          Seixas de Melo, J. Sérgio
          Amir, Elizabeta
          Rozen, Shlomo
        affil:
          Department of Physical Chemistry, University of Málaga, Campus de Teatinos s/n, Málaga 29071, Spain
          Steacie Institute for Molecular Sciences, National Research Council of Canada, 100 Sussex Drive, Ottawa, K1A 0R6 Canada
          Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109
          Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal
          School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978, Israel
      su:
        Thiophenes
        Electrons
        Optical properties
        Photoemission
        Density functionals
      sug:
        subj:
          Thiophenes
          Electrons
          Optical properties
          Photoemission
          Density functionals
      ab: A comprehensive photophysical and spectroscopic (electronic and Raman) study guided by density functional theory, DFT, CIS, and correlated ab initio calculations has been performed on a series of fully oxidized oligothiophenes with variable chain length, and up to four rings. A comparison with the properties of oligoenes and oligothiophenes is proposed. Absorption, fluorescence, lifetimes, flash-photolysis, phosphorescence, two-photon absorption, Raman, resonance Raman, and thermospectroscopy data are collected and interpreted according to the obtained theoretical results. The interest is focused on the ground electronic state and in the low-lying excited electronic states. Full oxygenation of the sulfur atoms of oligothiophenes results in: (i) restricted inter-ring isomerization such as observed from the absorption spectra; (ii) an effective quenching of fluorescence, and (iii) the appearance of dual emission. The emission features are explained by the interference of a dipole-allowed and a dipole-forbidden singlet excited states leading to simultaneous lighting from a local Frankel and an intramolecular charge transfer photon-releasing configurations. These two excited states contribute to the broadening of the light emission spectrum. These properties highlight the similarity of these samples to that of oligoenes with comparable number of π-electrons.
      pubtype: Academic Journal
      doctype: Article
      src: R
    language: English
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