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

研究成果: ジャーナルへの寄稿記事

抄録

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.

元の言語英語
記事番号3576
ジャーナルNature communications
10
発行部数1
DOI
出版物ステータス出版済み - 12 1 2019

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Protein Folding
Porphyrins
Molecules
Pharmaceutical Preparations
molecules
interactions
Protein folding
assembling
porphyrins
folding
proteins
Atoms
radii
Geometry
synthesis
geometry
atoms

All Science Journal Classification (ASJC) codes

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

これを引用

Nozawa, R., Kim, J., Oh, J., Lamping, A., Wang, Y., Shimizu, S., ... Shinokubo, H. (2019). Three-dimensional aromaticity in an antiaromatic cyclophane. Nature communications, 10(1), [3576]. https://doi.org/10.1038/s41467-019-11467-4

Three-dimensional aromaticity in an antiaromatic cyclophane. / Nozawa, Ryo; Kim, Jinseok; Oh, Juwon; Lamping, Anna; Wang, Yemei; Shimizu, Soji; Hisaki, Ichiro; Kowalczyk, Tim; Fliegl, Heike; Kim, Dongho; Shinokubo, Hiroshi.

:: Nature communications, 巻 10, 番号 1, 3576, 01.12.2019.

研究成果: ジャーナルへの寄稿記事

Nozawa, R, Kim, J, Oh, J, Lamping, A, Wang, Y, Shimizu, S, Hisaki, I, Kowalczyk, T, Fliegl, H, Kim, D & Shinokubo, H 2019, 'Three-dimensional aromaticity in an antiaromatic cyclophane', Nature communications, 巻. 10, 番号 1, 3576. https://doi.org/10.1038/s41467-019-11467-4
Nozawa, Ryo ; Kim, Jinseok ; Oh, Juwon ; Lamping, Anna ; Wang, Yemei ; Shimizu, Soji ; Hisaki, Ichiro ; Kowalczyk, Tim ; Fliegl, Heike ; Kim, Dongho ; Shinokubo, Hiroshi. / Three-dimensional aromaticity in an antiaromatic cyclophane. :: Nature communications. 2019 ; 巻 10, 番号 1.
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