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3,14-Bis(p-nitrophenyl)-17,17-dipentyltetrabenzo[a,c,g,i]-fluorene: A New Fluorophore Displaying Both Remarkable Solvatochromism and Crystalline-Induced Emission

Authors

  • Yoshiaki Ueda,

    1. Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo 671-2280 (Japan)
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  • Yusuke Tanigawa,

    1. Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo 671-2280 (Japan)
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  • Prof. Chitoshi Kitamura,

    1. Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo 671-2280 (Japan)
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  • Prof. Hiroshi Ikeda,

    Corresponding author
    1. Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531 (Japan)
    • Hiroshi Ikeda, Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531 (Japan)

      Takeshi Kawase, Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo 671-2280 (Japan)

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  • Yuichi Yoshimoto,

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

    1. Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531 (Japan)
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  • Prof. Kazuhiko Mizuno,

    1. Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531 (Japan)
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  • Prof. Hiroyuki Kurata,

    1. Department of Chemistry, Graduate School of Science, Osaka University, Machikaneyama-cho 1-1, Toyonaka, Osaka 560-0043 (Japan)
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  • Prof. Takeshi Kawase

    Corresponding author
    1. Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo 671-2280 (Japan)
    • Hiroshi Ikeda, Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531 (Japan)

      Takeshi Kawase, Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo 671-2280 (Japan)

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Abstract

A series of 17,17-dialkyl-3,14-diaryltetrabenzofluorenes were efficiently prepared by using Suzuki–Miyaura cross-coupling reactions of the corresponding 3,14-dibromo derivatives. Studies of the unique fluorescence properties of these compounds showed that they display intense blue to yellow fluorescence with high quantum yields in the solution state and blue to orange fluorescence with moderate quantum yields in the solid state. In addition, the fluorescence wavelength of the bis(p-nitrophenyl) derivative is remarkably solvent-dependent in a manner that correlates with the solvent polarity parameter ET(30). The results of density function theory calculations suggest that the intramolecular charge-transfer character of the HOMO–LUMO transition is responsible for the large solvent effect. Moreover, addition of water to a tetrahydrofuran (THF) solution of this compound leads to quenching of the yellow fluorescence owing to an increase in the solvent polarity. However, when the amount of water fraction exceeds 70 %, a new fluorescence band appears at the same orange-red emission wavelength as that of the solid-state fluorescence. This observation suggests the occurrence of a crystallization-induced emission (CIE) phenomenon in highly aqueous THF.

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