Understanding optoelectronic properties of cyano-terminated oligothiophenes in the context of intramolecular charge transfer

Sandra Rodríguez González, Jesús Orduna, Raquel Alicante, Belén Villacampa, Kari A. McGee, João Pina, J. Seixas De Melo, Kathryn M. Schwaderer, Jared C. Johnson, Brady A. Blackorbay, Jacob J. Hansmeier, Victoria F. Bolton, Tyler J. Helland, Brett A. Edlund, Ted M. Pappenfus, Juan T. López Navarrete, Juan Casado

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17 Scopus citations

Abstract

In this paper we have prepared a new series of oligothiophenes capped with hexyl groups and a variety of strong acceptors, mainly cyanovinyl moieties. An exhaustive analysis of the absorption, photophysical, electrochemical, solid state, nonlinear optical and vibrational properties has been presented guided by theoretical calculations. The investigation is centered on the efficiency of the intramolecular charge transfer (i.e., chain length and acceptor dependence) and its impact on all the relevant electronic, structural, optical, and vibrational properties. The most significant features imparted by the acceptors through the π-conjugated oligothiophene path are (i) intense visible electronic absorptions, (ii) tuned fluorescence wavelength emissions, (iii) solid state π-stacking, (iv) ambipolar redox behavior, (v) S1 ? S0 internal conversion as being the major route for the deactivation of the excited state, and (vi) large electronic and vibrational contributions to their nonlinear optical response (hyperpolarizability). The analysis establishes connections between the different properties of the materials and structure-function relationships useful in organic electronics.

Original languageEnglish (US)
Pages (from-to)10573-10585
Number of pages13
JournalJournal of Physical Chemistry B
Volume115
Issue number36
DOIs
StatePublished - Sep 15 2011
Externally publishedYes

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    González, S. R., Orduna, J., Alicante, R., Villacampa, B., McGee, K. A., Pina, J., Seixas De Melo, J., Schwaderer, K. M., Johnson, J. C., Blackorbay, B. A., Hansmeier, J. J., Bolton, V. F., Helland, T. J., Edlund, B. A., Pappenfus, T. M., López Navarrete, J. T., & Casado, J. (2011). Understanding optoelectronic properties of cyano-terminated oligothiophenes in the context of intramolecular charge transfer. Journal of Physical Chemistry B, 115(36), 10573-10585. https://doi.org/10.1021/jp2070375