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 () and Hiroshi Shinokubo ()
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Ryo Nozawa: Nagoya University
Jinseok Kim: Yonsei University
Juwon Oh: Yonsei University
Anna Lamping: Western Washington University
Yemei Wang: Kyushu University
Soji Shimizu: Kyushu University
Ichiro Hisaki: Hokkaido University
Tim Kowalczyk: Western Washington University
Heike Fliegl: Institute of Nanotechnology
Dongho Kim: Yonsei University
Hiroshi Shinokubo: Nagoya University

Nature Communications, 2019, vol. 10, issue 1, 1-7

Abstract: Abstract 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.

Date: 2019
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DOI: 10.1038/s41467-019-11467-4

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