Synthesis, spectroscopy, nonlinear optics, and theoretical investigations of thienylethynyl octopoles with a tunable core

María Moreno Oliva, Juan Casado*, Juan T.López Navarrete, Gunther Hennrich, Stijn Van Cleuvenbergen, Inge Asselberghs, Koen Clays, M. Carmen Ruiz Delgado, Jean-Luc Bredas, J. Sérgio Seixas De Melo, Luisa De Cola

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)8223-8234
Number of pages12
JournalChemistry - A European Journal
Volume15
Issue number33
DOIs
StatePublished - Aug 17 2009

Keywords

  • Density functional calculations
  • Donor-acceptor systems
  • Nonlinear optics
  • Phosphorescence
  • Sulfur heterocycles

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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