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Cooperative effects of o - and m -methyl groups on the intramolecular charge-transfer emission properties of dibenzoylmethanatoboron difluorides

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Abstract

The photophysical properties of o -tolyl-, m -tolyl-, and p -xylyl-substituted asymmetric diaroylmethanatoboron difluorides in a mixture of CH2Cl2 and c -C6H12, and in the crystalline state were determined. In solution, the fluorescence (FL) properties of these substances are controlled by the position and number of methyl groups on the phenyl rings. An especially interesting finding is that FL from the p -xylyl derivative occurs from an excited state which possesses intramolecular charge-transfer character caused by the o - and m -methyl groups cooperatively. The results of X-ray crystallographic analysis reveal that these asymmetric diaroylmethanatoboron difluorides form dyads through orbital overlap of neighboring molecules. This phenomenon governs the unique FL properties of these substances in the solid state.

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Authors and Affiliations

  1. Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka, 599-8531, Japan

    Mirai Tanaka, Shunsuke Muraoka, Yasunori Matsui, Takuya Ogaki, Kazuhiko Mizuno & Hiroshi Ikeda

  2. The Research Institute for Molecular Electronic Devices (RIMED), Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka, 599-8531, Japan

    Yasunori Matsui, Eisuke Ohta, Takuya Ogaki & Hiroshi Ikeda

Authors
  1. Mirai Tanaka
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  2. Shunsuke Muraoka
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  3. Yasunori Matsui
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  4. Eisuke Ohta
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  5. Takuya Ogaki
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  6. Kazuhiko Mizuno
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  7. Hiroshi Ikeda
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Correspondence to Hiroshi Ikeda.

Additional information

Electronic supplementary information (ESI) available. CCDC 1524227, 1524230 and 1524228. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7pp00005g

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Tanaka, M., Muraoka, S., Matsui, Y. et al. Cooperative effects of o - and m -methyl groups on the intramolecular charge-transfer emission properties of dibenzoylmethanatoboron difluorides. Photochem Photobiol Sci 16, 845–853 (2017). https://doi.org/10.1039/c7pp00005g

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  • DOI: https://doi.org/10.1039/c7pp00005g

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