Influence of Chromophore Length and Acceptor Groups on the Optical Properties of Rigidified Merocyanine Dyes

Authors

  • Katharina Christina Kreß,

    1. Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart (Germany), Fax: (+49) 771-685-64285
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  • Dr. Thomas Fischer,

    1. Fraunhofer-Institut für Angewandte Polymerforschung, Bereich Funktionale Polymersysteme, Geiselbergstrasse 69, 14476 Potsdam-Golm (Germany), Fax: (+49) 331-568-3259
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  • Dr. Joachim Stumpe,

    1. Fraunhofer-Institut für Angewandte Polymerforschung, Bereich Funktionale Polymersysteme, Geiselbergstrasse 69, 14476 Potsdam-Golm (Germany), Fax: (+49) 331-568-3259
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  • Dr. Wolfgang Frey,

    1. Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart (Germany), Fax: (+49) 771-685-64285
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  • Dr. Melanie Raith,

    1. Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart (Germany), Fax: (+49) 771-685-64285
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  • Omid Beiraghi,

    1. Department of Chemistry and Biochemistry, University of Windsor, Windsor, ON, N9B 3P4 (Canada), Fax: (+1) 519-973-7098
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  • Prof. Dr. S. Holger Eichhorn,

    Corresponding author
    1. Department of Chemistry and Biochemistry, University of Windsor, Windsor, ON, N9B 3P4 (Canada), Fax: (+1) 519-973-7098
    • S. Holger Eichhorn, Department of Chemistry and Biochemistry, University of Windsor, Windsor, ON, N9B 3P4 (Canada), Fax: (+1) 519-973-7098

      Sabine Laschat, Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart (Germany), Fax: (+49) 771-685-64285

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  • Dr. Stefan Tussetschläger,

    1. Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart (Germany), Fax: (+49) 771-685-64285
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  • Prof. Dr. Sabine Laschat

    Corresponding author
    1. Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart (Germany), Fax: (+49) 771-685-64285
    • S. Holger Eichhorn, Department of Chemistry and Biochemistry, University of Windsor, Windsor, ON, N9B 3P4 (Canada), Fax: (+1) 519-973-7098

      Sabine Laschat, Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart (Germany), Fax: (+49) 771-685-64285

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Abstract

Three series of rigidified tri-, penta- and heptamethine merocyanine dyes were synthesised. A piperidyl moiety was chosen as the electron-donating substituent while the electron-accepting group was varied from ketones to malononitriles and cyanoacetates. The structures of the compounds in the solid state and in solution were elucidated by X-ray diffraction and NMR spectroscopy, respectively, while optical properties were investigated by absorption and emission spectroscopy. As a general trend, the acceptor properties decrease in the series malononitrile>cyanoacetate>ketone based on the analysis of their solvatochromic behaviour. The experimental results were further supported by calculations at the B3LYP 6-311+G(d) level of theory.

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