Three-dimensional aromaticity in an antiaromatic cyclophane

Ryo Nozawa, Jinseok Kim, Juwon Oh, Anna Lamping, Yemei Wang, Soji Shimizu, Ichiro Hisaki, Tim Kowalczyk, Heike Fliegl, Dongho Kim, Hiroshi Shinokubo

    Research output: Contribution to journalArticlepeer-review

    52 Citations (Scopus)


    Understanding of interactions among molecules is essential to elucidate the binding of pharmaceuticals on receptors, the mechanism of protein folding and self-assembling of organic molecules. While interactions between two aromatic molecules have been examined extensively, little is known about the interactions between two antiaromatic molecules. Theoretical investigations have predicted that antiaromatic molecules should be stabilized when they stack with each other by attractive intermolecular interactions. Here, we report the synthesis of a cyclophane, in which two antiaromatic porphyrin moieties adopt a stacked face-to-face geometry with a distance shorter than the sum of the van der Waals radii of the atoms involved. The aromaticity in this cyclophane has been examined experimentally and theoretically. This cyclophane exhibits three-dimensional spatial current channels between the two subunits, which corroborates the existence of attractive interactions between two antiaromatic π-systems.

    Original languageEnglish
    Article number3576
    JournalNature communications
    Issue number1
    Publication statusPublished - Dec 1 2019

    All Science Journal Classification (ASJC) codes

    • Chemistry(all)
    • Biochemistry, Genetics and Molecular Biology(all)
    • Physics and Astronomy(all)


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