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Synthesis, Crystal Structures, and Properties of 6,12-Diaryl-Substituted Indeno[1,2-b]fluorenes

Authors

  • Dr. Jun-ichi Nishida,

    1. Department of Electronic Chemistry, Interdisciplinary Graduate School of Science and Engineering, Tokyo Institute of Technology, 4259, Nagatsuta, Midori-ku, Yokohama 226-8502 (Japan), Fax: (+81) 45-924-5489
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  • Shingo Tsukaguchi,

    1. Department of Electronic Chemistry, Interdisciplinary Graduate School of Science and Engineering, Tokyo Institute of Technology, 4259, Nagatsuta, Midori-ku, Yokohama 226-8502 (Japan), Fax: (+81) 45-924-5489
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  • Prof. Dr. Yoshiro Yamashita

    Corresponding author
    1. Department of Electronic Chemistry, Interdisciplinary Graduate School of Science and Engineering, Tokyo Institute of Technology, 4259, Nagatsuta, Midori-ku, Yokohama 226-8502 (Japan), Fax: (+81) 45-924-5489
    • Department of Electronic Chemistry, Interdisciplinary Graduate School of Science and Engineering, Tokyo Institute of Technology, 4259, Nagatsuta, Midori-ku, Yokohama 226-8502 (Japan), Fax: (+81) 45-924-5489
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Abstract

Fused polycyclic indeno[1,2-b]fluorene derivatives with aryl substituents at the 6,12-positions have been prepared as a potential antiaromatic 20π electronic system. They showed strong absorptions in the visible region and amphoteric redox properties. The quinoid-type molecular structures were revealed by X-ray crystal-structure analysis, which indicated that the bond lengths of the quinoid unit depend on the aryl substituents. Whereas nucleus-independent chemical shift NICS(1) calculations indicate the antiaromatic nature of the s-indacene core, they have higher stability than substituted acene derivatives. The derivatives with difluorophenyl or anthryl groups were stable in solution. Vapor-deposited thin films showed ambipolar carrier transportation in the field-effect transistor devices.

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