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Emission and transient absorption measurements of substitution effects of C–C triple bonds on relaxation processes of the fluorescent state of naphthalenes

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Abstract

Photophysical and photochemical properties of naphthalenes substituted with trimethylsilylethynyl, tert-butylethynyl, and trimethylsilylbutadiynyl groups were investigated by measurement of fluorescence yields, lifetimes, and triplet absorption. Introducing trimethylsilylethynyl and tert-butylethynyl groups to the 1-position of the naphthalene skeleton substantially enhanced fluorescence and intersystem crossing (ISC). The rates of fluorescence of 2-substituted naphthalenes were low. The effect of ethynyl groups on the 1-substituted naphthalenes was rationalized in terms of an increase of the transition moment along the short axis of the naphthalene skeleton. Substitution of the trimethylsilylbutadiynyl group at the 1 or 2-position of the naphthalene skeleton caused a considerable decrease in the fluorescence yield (approximately 0.01) and an increase in the ISC yield (0.99).

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Author notes

  1. Hajime Maeda

    Present address: Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kanazawa, 920-1192, Japan

Authors and Affiliations

  1. Department of Chemistry and Chemical Biology, Graduate School of Engineering, Gunma University, Kiryu, Gunma, 376-8515, Japan

    Minoru Yamaji

  2. Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, Sakai, Osaka, 599-8531, Japan

    Hajime Maeda, Keita Minamida, Tomohiro Maeda & Kazuhiko Mizuno

  3. Graduate School of Science and Engineering, Tokyo Institute of Technology Ookayama, Meguro-ku, Tokyo, 152-8552, Japan

    Kengo Asai & Gen-Ichi Konishi

Authors
  1. Minoru Yamaji
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  2. Hajime Maeda
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  3. Keita Minamida
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  4. Tomohiro Maeda
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  5. Kengo Asai
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  6. Gen-Ichi Konishi
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  7. Kazuhiko Mizuno
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Corresponding authors

Correspondence to Minoru Yamaji, Hajime Maeda or Kazuhiko Mizuno.

Additional information

This article is dedicated to Professor Kazuhiko Mizuno on his retirement.

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Yamaji, M., Maeda, H., Minamida, K. et al. Emission and transient absorption measurements of substitution effects of C–C triple bonds on relaxation processes of the fluorescent state of naphthalenes. Res Chem Intermed 39, 321–345 (2013). https://doi.org/10.1007/s11164-012-0652-4

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  • DOI: https://doi.org/10.1007/s11164-012-0652-4

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