An Extremely Redox-Active Air-Stable Neutral π Radical: Dicyanomethylene-Substituted Triangulene with a Threefold Symmetry

Authors

  • Dr. Akira Ueda,

    1. Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043 (Japan), Fax: (+81) 6-6850-5395
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  • Hideki Wasa,

    1. Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043 (Japan), Fax: (+81) 6-6850-5395
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  • Dr. Shinsuke Nishida,

    1. Department of Chemistry and Molecular Materials Science, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585 (Japan), Fax: (+81) 6-6605-2522
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  • Dr. Yuki Kanzaki,

    1. Department of Chemistry and Molecular Materials Science, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585 (Japan), Fax: (+81) 6-6605-2522
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  • Prof. Dr. Kazunobu Sato,

    1. Department of Chemistry and Molecular Materials Science, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585 (Japan), Fax: (+81) 6-6605-2522
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  • Prof. Dr. Daisuke Shiomi,

    1. Department of Chemistry and Molecular Materials Science, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585 (Japan), Fax: (+81) 6-6605-2522
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  • Prof. Dr. Takeji Takui,

    Corresponding author
    1. Department of Chemistry and Molecular Materials Science, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585 (Japan), Fax: (+81) 6-6605-2522
    • Takeji Takui, Department of Chemistry and Molecular Materials Science, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585 (Japan), Fax: (+81) 6-6605-2522===

      Yasushi Morita, Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043 (Japan), Fax: (+81) 6-6850-5395===

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  • Prof. Dr. Yasushi Morita

    Corresponding author
    1. Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043 (Japan), Fax: (+81) 6-6850-5395
    • Takeji Takui, Department of Chemistry and Molecular Materials Science, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585 (Japan), Fax: (+81) 6-6605-2522===

      Yasushi Morita, Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043 (Japan), Fax: (+81) 6-6850-5395===

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Abstract

original image

Radically active: A redox-active air-stable neutral π radical (1.) with three dicyanomethylene groups introduced with threefold symmetry into a triangulene π skeleton instead of the oxygen atoms of TOT. was designed, synthesized, and characterized (see figure). The enhanced electron-accepting ability and extended π-electronic system of this chemical modification gave an extremely small SOMO–LUMO gap and significantly lowered the frontier orbital energies, leading to the remarkable increase in the redox stages.

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