Oligothiophene Tetracyanobutadienes: Alternative Donor-Acceptor Architectures for Molecular and Polymeric Materials (Articolo in rivista)

Type
Label
  • Oligothiophene Tetracyanobutadienes: Alternative Donor-Acceptor Architectures for Molecular and Polymeric Materials (Articolo in rivista) (literal)
Anno
  • 2011-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1021/cm102128g (literal)
Alternative label
  • Pappenfus T.M.; Schneiderman D.K.; Casado J.; Navarrete J.T.L.; Delgado M.C.R.; Zotti G.; Vercelli B.; Lovander M.D.; Hinkle L.M.; Bohnsack J.N.; Mann K.R. (2011)
    Oligothiophene Tetracyanobutadienes: Alternative Donor-Acceptor Architectures for Molecular and Polymeric Materials
    in Chemistry of materials
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Pappenfus T.M.; Schneiderman D.K.; Casado J.; Navarrete J.T.L.; Delgado M.C.R.; Zotti G.; Vercelli B.; Lovander M.D.; Hinkle L.M.; Bohnsack J.N.; Mann K.R. (literal)
Pagina inizio
  • 823 (literal)
Pagina fine
  • 831 (literal)
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  • http://pubs.acs.org/doi/abs/10.1021/cm102128g (literal)
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  • 23 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 3 (literal)
Note
  • Scopu (literal)
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • 1,2,8 : Division of Science and Mathematics, University of Minnesota, Morris, MN 56267, United States / 3-5 : Department of Physical Chemistry, University of Málaga, Campus de Teatinos s/n, Málaga 29071, Spain / 6,7 : Istituto CNR per l'Energetica e le Interfasi, C.o. Stati Uniti 4, 35127 Padova, Italy / 9-11 : Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, United States (literal)
Titolo
  • Oligothiophene Tetracyanobutadienes: Alternative Donor-Acceptor Architectures for Molecular and Polymeric Materials (literal)
Abstract
  • Oligothiophene-substituted 1,1,4,4-tetracyanobutadienes (TCBDs) have been synthesized by [2þ 2] cycloaddition reactions between tetracyanoethylene and oligothiophene alkynes. The TCBD moiety is compared to other electron acceptors attached to dibutylterthiophene including dicyanovinyl (DCV) and tricyanovinyl (TCV).These donor-acceptor molecules (TCBD-3T, DCV-3T, andTCV-3T) show red-shifted absorption spectra relative to the unsubstituted oligothiophene as a result of intramolecular charge-transfer (ICT). Monosubstituted terthiophenes bearing the electron acceptors show both oxidation and reduction processes as characterized by cyclic voltammetry. Density functional theory (DFT) calculations are used to explain the electronic and redox properties of the materials. Electrochemical oxidation of a bis(terthienyl)-substitutedTCBDmolecule (3T-TCBD-3T) yields a conducting polymer exhibiting balanced ambipolar redox conduction with similar values for the oxidized and reduced states of the polymer (1 _ 10-3 S cm-1). Raman spectra of the asymmetric donor-acceptor materials are characterized by two intense bands characteristic of the aromatic and quinoidal regions in the conjugated À-system of the oligothiophene. (literal)
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