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Synthesis, Photophysics and Nonlinear Optical Properties of Stilbenoid Pyrimidine-Based Dyes Bearing Methylenepyran Donor Groups

Authors

  • Dr. Sylvain Achelle,

    Corresponding author
    1. Institut des Sciences Chimiques de Rennes, UMR CNRS 6226, IUT de Lannion rue Edouard Branly, BP 30219, 22302 Lannion Cedex (France)
    • Institut des Sciences Chimiques de Rennes, UMR CNRS 6226, IUT de Lannion rue Edouard Branly, BP 30219, 22302 Lannion Cedex (France)
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  • Dr. Jean-Pierre Malval,

    Corresponding author
    1. Institut de Science des Matériaux de Mulhouse, UMR CNRS 7361, Université de Haute-Alsace, 15 rue Jean Starcky ,68057 Mulhouse (France)
    • Institut de Science des Matériaux de Mulhouse, UMR CNRS 7361, Université de Haute-Alsace, 15 rue Jean Starcky ,68057 Mulhouse (France)
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  • Dr. Stéphane Aloïse,

    1. Laboratoire de Spectrochimie Infrarouge et Raman, UMR CNRS 8516, Université des Sciences et Technologies de Lille, 59655 Villeneuve d'Ascq Cedex (France)
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  • Dr. Alberto Barsella,

    1. Département d'Optique ultra-rapide et Nanophotonique, IPCMS-CNRS 23 Rue du Loess, BP 43, 67034 Strasbourg Cedex 2 (France)
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  • Dr. Arnaud Spangenberg,

    1. Institut de Science des Matériaux de Mulhouse, UMR CNRS 7361, Université de Haute-Alsace, 15 rue Jean Starcky ,68057 Mulhouse (France)
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  • Dr. Loic Mager,

    1. Département d'Optique ultra-rapide et Nanophotonique, IPCMS-CNRS 23 Rue du Loess, BP 43, 67034 Strasbourg Cedex 2 (France)
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  • Dr. Huriye Akdas-Kilig,

    1. Institut des Sciences Chimiques de Rennes UMR CNRS 6226, Campus de Beaulieu, 263 av. du Général Leclerc, 35042 Rennes (France)
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  • Dr. Jean-Luc Fillaut,

    1. Institut des Sciences Chimiques de Rennes UMR CNRS 6226, Campus de Beaulieu, 263 av. du Général Leclerc, 35042 Rennes (France)
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  • Prof. Bertrand Caro,

    1. Institut des Sciences Chimiques de Rennes, UMR CNRS 6226, IUT de Lannion rue Edouard Branly, BP 30219, 22302 Lannion Cedex (France)
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  • Prof. Françoise Robin-le Guen

    1. Institut des Sciences Chimiques de Rennes, UMR CNRS 6226, IUT de Lannion rue Edouard Branly, BP 30219, 22302 Lannion Cedex (France)
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Abstract

The nonlinear properties and the photophysical behavior of two π-conjugated chromophores that incorporate an electron-deficient pyrimidine core (A) and γ-methylenepyrans as terminal donor (D) groups have been thoroughly investigated. Both dipolar and quadrupolar branching strategies are explored and rationalized on the basis of the Frenkel exciton model. Even though a cooperative effect is clearly observed if the dimensionality is increased, the nonlinear optical (NLO) response of this series is moderate if one considers the nature of the D/A couple and the size of the chromophores (as measured by the number of π electrons). This effect was attributed to a disruption in the electronic conjugation within the dyes’ scaffold for which the geometry deviates from planarity owing to a noticeable twisting of the pyranylidene end-groups. This latter structural parameter also has a strong influence on the excited-state dynamics, which leads to a very efficient fluorescence quenching.

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