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Elucidation of π-Conjugation Modes in Diarene-Fused 1,2-Dihydro-1,2-diborin Dianions

Authors

  • Takafumi Araki,

    1. Department of Chemistry, Graduate School of Science, Nagoya University and CREST, Japan Science and Technology Agency, Furo, Chikusa, Nagoya, 464-8602 (Japan), Fax: (+81) 52-789-5947
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  • Prof. Dr. Atsushi Wakamiya,

    Corresponding author
    1. Institute for Chemical Research, Kyoto University and PRESTO, Japan Science and Technology Agency, Gokasyo, Uji, Kyoto, 611-0011 (Japan), Fax: (+81) 774-38-3178
    • Atsushi Wakamiya, Institute for Chemical Research, Kyoto University and PRESTO, Japan Science and Technology Agency, Gokasyo, Uji, Kyoto, 611-0011 (Japan), Fax: (+81) 774-38-3178

      Shigehiro Yamaguchi, Department of Chemistry, Graduate School of Science, Nagoya University and CREST, Japan Science and Technology Agency, Furo, Chikusa, Nagoya, 464-8602 (Japan), Fax: (+81) 52-789-5947

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  • Kenji Mori,

    1. Department of Chemistry, Graduate School of Science, Nagoya University and CREST, Japan Science and Technology Agency, Furo, Chikusa, Nagoya, 464-8602 (Japan), Fax: (+81) 52-789-5947
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  • Prof. Dr. Shigehiro Yamaguchi

    Corresponding author
    1. Department of Chemistry, Graduate School of Science, Nagoya University and CREST, Japan Science and Technology Agency, Furo, Chikusa, Nagoya, 464-8602 (Japan), Fax: (+81) 52-789-5947
    • Atsushi Wakamiya, Institute for Chemical Research, Kyoto University and PRESTO, Japan Science and Technology Agency, Gokasyo, Uji, Kyoto, 611-0011 (Japan), Fax: (+81) 774-38-3178

      Shigehiro Yamaguchi, Department of Chemistry, Graduate School of Science, Nagoya University and CREST, Japan Science and Technology Agency, Furo, Chikusa, Nagoya, 464-8602 (Japan), Fax: (+81) 52-789-5947

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Abstract

A series of diarene-fused 1,2-dihydro-1,2-diborins were prepared as a new B[BOND]B-bond-embedded polycyclic π-electron system. The reduction of these compounds with metals produced their corresponding dianions, the π-conjugation modes of which varied from 6π-conjugation within the central 1,2-diborin skeleton to 14π peripheral conjugation over the tricyclic skeleton, depending on the nature of the reduced biaryl framework. Moreover, the countercation to the dianions had a significant effect on the absorption spectra, with a dramatic color change from yellow to deep blue, depending on the distance between the tricyclic dianion skeleton and the countercation.

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