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Synthesis, Spectroscopy, Nonlinear Optics, and Theoretical Investigations of Thienylethynyl Octopoles with a Tunable Core

Oliva, María Moreno ; Casado, Juan ; López Navarrete, Juan T. ; Hennrich, Gunther ; van Cleuvenbergen, Stijn ; Asselberghs, Inge ; Clays, Koen ; Ruiz Delgado, M. Carmen ; Brédas, Jean‐Luc ; Seixas de Melo, J. Sérgio ; De Cola, Luisa

Chemistry : a European journal, 2009-08, Vol.15 (33), p.8223-8234 [Periódico revisado por pares]

Weinheim: WILEY‐VCH Verlag

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  • Título:
    Synthesis, Spectroscopy, Nonlinear Optics, and Theoretical Investigations of Thienylethynyl Octopoles with a Tunable Core
  • Autor: Oliva, María Moreno ; Casado, Juan ; López Navarrete, Juan T. ; Hennrich, Gunther ; van Cleuvenbergen, Stijn ; Asselberghs, Inge ; Clays, Koen ; Ruiz Delgado, M. Carmen ; Brédas, Jean‐Luc ; Seixas de Melo, J. Sérgio ; De Cola, Luisa
  • Assuntos: density functional calculations ; donor–acceptor systems ; nonlinear optics ; phosphorescence ; sulfur heterocycles
  • É parte de: Chemistry : a European journal, 2009-08, Vol.15 (33), p.8223-8234
  • Notas: ObjectType-Article-1
    SourceType-Scholarly Journals-1
    ObjectType-Feature-2
    content type line 23
  • Descrição: We have synthesized three new molecules that have three thienylethynyl arms substituting a central benzene core and different electron donor/acceptor groups in the three remaining phenyl positions. The absorption, fluorescence, phosphorescence, and transient triplet–triplet spectra are analyzed in the light of the electronic structure of the ground and excited states obtained from quantum‐chemical calculations. From the above, the relevant photophysical data (including quantum yields, lifetimes, and rate constants) could be derived. It was found that the major deactivation pathway is internal conversion, which competes with the fluorescence and intersystem crossing processes. For the three investigated compounds, we provide convincing theoretical support corroborating these findings and further conclusions based on the theoretical information obtained. These molecules are one of the very few cases in which the depolarization ratios, obtained from the NLO optical measurements, clearly reflect the octopolar configuration. Molecular hyperpolarizabilities have been measured and display a typical dependence on the donor–acceptor substitution pattern. A fine tune! The ability to tune molecular properties by ad hoc organic synthesis permits fine control of the optical response of organic molecules used in plastic electronics (see figure). However, this requires a previous diagnosis of the key factors that decide the electro‐optical output. This work represents such an example and describes interesting phosphorescence and NLO properties emerging from their particular octopolar symmetry.
  • Editor: Weinheim: WILEY‐VCH Verlag
  • Idioma: Inglês
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  • Realização: ABCD-USP USP   Logos de Redes Sociais: Freepik

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