Stacked antiaromatic porphyrins

Ryo Nozawa, Hiroko Tanaka, Won Young Cha, Yongseok Hong, Ichiro Hisaki, Soji Shimizu, Ji Young Shin, Tim Kowalczyk, Stephan Irle, Dongho Kim, Hiroshi Shinokubo

    研究成果: ジャーナルへの寄稿学術誌査読

    89 被引用数 (Scopus)

    抄録

    Aromaticity is a key concept in organic chemistry. Even though this concept has already been theoretically extrapolated to three dimensions, it usually still remains restricted to planar molecules in organic chemistry textbooks. Stacking of antiaromatic π-systems has been proposed to induce three-dimensional aromaticity as a result of strong frontier orbital interactions. However, experimental evidence to support this prediction still remains elusive so far. Here we report that close stacking of antiaromatic porphyrins diminishes their inherent antiaromaticity in the solid state as well as in solution. The antiaromatic stacking furthermore allows a delocalization of the π-electrons, which enhances the two-photon absorption cross-section values of the antiaromatic porphyrins. This feature enables the dynamic switching of the non-linear optical properties by controlling the arrangement of antiaromatic π-systems on the basis of intermolecular orbital interactions.

    本文言語英語
    論文番号13620
    ジャーナルNature communications
    7
    DOI
    出版ステータス出版済み - 11月 30 2016

    !!!All Science Journal Classification (ASJC) codes

    • 化学 (全般)
    • 生化学、遺伝学、分子生物学(全般)
    • 物理学および天文学(全般)

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