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Fluorescence photoswitching of a diarylethene-perylenebisimide dyad based on intramolecular electron transfer

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Abstract

A fluorescent photochromic molecule, which is composed of a photochromic diarylethene (DE) and a fluorescent perylenebisimide (PBI), was synthesized and its fluorescence photoswitching was studied. The fluorescence quantum yield of the open-ring isomer is constant irrespective of solvent polarity, while that of the closed-ring isomer decreases with an increase in the dielectric constant of solvents. Femtosecond time-resolved transient and fluorescence lifetime measurements revealed that the fluorescence quenching of the closed-ring isomer is attributed to the intramolecular electron transfer from the PBIchromophore to the DE unit.

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Authors and Affiliations

  1. Research Institute for Electronic Science, Hokkaido University, N20, W10, Kita-ku, Sapporo, 001-0020, Japan

    Tuyoshi Fukaminato & Nobuyuki Tamaoki

  2. PREST, Japan Science and Technology Agency (JST), Japan

    Tuyoshi Fukaminato

  3. Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Motooka 744, Nishi-ku, Fukuoka, 819-0395, Japan

    Masaaki Tanaka & Takao Doi

  4. Division of Frontier Materials Science, Graduate School of Engineering Science, and Center for Quantum Science and Technology under Extreme Conditions, Osaka University, Toyonaka, Osaka, 560-8531, Japan

    Tetsuro Katayama, Arabinda Mallick, Yukihide Ishibashi & Hiroshi Miyasaka

  5. Department of Chemistry and Research Center for Smart Molecules, Rikkyo University, Nishi-Ikebukuro 3-34-1, Toshima-ku, Tokyo, 171-8501, Japan

    Masahiro Irie

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  1. Tuyoshi Fukaminato
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  2. Masaaki Tanaka
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  3. Takao Doi
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  4. Nobuyuki Tamaoki
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  5. Tetsuro Katayama
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  6. Arabinda Mallick
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  7. Yukihide Ishibashi
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  8. Hiroshi Miyasaka
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  9. Masahiro Irie
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Corresponding authors

Correspondence to Tuyoshi Fukaminato, Hiroshi Miyasaka or Masahiro Irie.

Additional information

This paper is part of a themed issue on synthetic and natural photoswitches.

Electronic supplementary information (ESI) available: Synthetic procedures, cyclic voltammograms and analysis of the transient absorption spectrum. See DOI: 10.1039/b9pp00131j

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Fukaminato, T., Tanaka, M., Doi, T. et al. Fluorescence photoswitching of a diarylethene-perylenebisimide dyad based on intramolecular electron transfer. Photochem Photobiol Sci 9, 181–187 (2010). https://doi.org/10.1039/b9pp00131j

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  • DOI: https://doi.org/10.1039/b9pp00131j

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