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Investigation of the photoisomerisation process in four p-benzoxazoyl-substituted stilbenes

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Abstract

Fluorescence properties and trans-cisphotoisomerisation of the benzoxazole derivatives 2-[4-(E)-(styryl)phenyl]benzoxazole (I), 2-{4-[(E)-2-(4-methoxyphenyl)vinyl]phenyl}benzoxazole (II), {4-[(E)-2-(4-benzoxazol-2-yl-phenyl)vinyl]phenyl}dimethylamine (III) and {4-[(E)-2-(4-benzoxazol-2-yl-phenyl)vinyl]phenyl}diphenylamine (IV) have been investigated in solvents of different polarities. It was found that these compounds exhibit efficient fluorescence with quantum yields and lifetimes strongly dependent on solvent polarity, although only compounds III and IV possess a significant charge transfer character in solvents of medium and high polarities. In addition, the photoisomerisation quantum efficiency depends strongly on the substitution of the phenyl ring in the electron donor moiety. A strong dependence of the quantum efficiency of the photoisomerisation on solvent was established. That quantity depends linearly on the non-radiative quantum yield of the deactivation of the excited singlet state for all investigated compounds. These results are consistent with a singlet state mechanism of the photoprocess. For compounds III and IV, with strong electron donors (N,N-dimethylaniline and triphenylamine), the molecule in the excited state trans configuration is more stabilized by solvent polarity than in the perpendicular form which causes more efficient isomerisation in nonpolar solvents. For compounds I and II the energy of the perpendicular configuration decreases more rapidly than that of the trans configuration when solvent polarity increases. In this case the energy barrier decreases with increasing solvent polarity. This makes the photoisomerisation process easier in polar solvents.

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Authors and Affiliations

  1. Faculty of Chemistry, Jagiellonian University, 30-060, Kraków, Ingardena 3, Poland

    Marek Mac, Tomasz Uchacz, Sabina Gorycka, Katarzyna Górz & Sebastian Leśniewski

  2. Department of Chemistry, University of Agriculture, 31-149, Kraków, Balicka 122, Poland

    Andrzej Danel & Ewa Kulig

Authors
  1. Marek Mac
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  2. Andrzej Danel
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  3. Tomasz Uchacz
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  4. Sabina Gorycka
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  5. Katarzyna Górz
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  6. Sebastian Leśniewski
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  7. Ewa Kulig
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Additional information

Electronic supplementary information (ESI) available: Fluorescence and trans-cis photoisomerisation data of the investigated compounds in solvents of different polarities; Fischer analysis for determination of the absorption spectum of the cis isomer. See DOI: 10.1039/b9pp00098d

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Mac, M., Danel, A., Uchacz, T. et al. Investigation of the photoisomerisation process in four p-benzoxazoyl-substituted stilbenes. Photochem Photobiol Sci 9, 357–364 (2010). https://doi.org/10.1039/b9pp00098d

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  • DOI: https://doi.org/10.1039/b9pp00098d

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