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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

Abstract (englisch):
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.

Verlagsausgabe §
DOI: 10.5445/IR/1000097657
Veröffentlicht am 20.08.2019
DOI: 10.1038/s41467-019-11467-4
Zitationen: 23
Zitationen: 29
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Nanotechnologie (INT)
Publikationstyp Zeitschriftenaufsatz
Publikationsmonat/-jahr 12.2019
Sprache Englisch
Identifikator ISSN: 2041-1723
KITopen-ID: 1000097657
HGF-Programm 43.21.04 (POF III, LK 01) Molecular Engineering
Erschienen in Nature Communications
Verlag Nature Research
Band 10
Heft 1
Seiten Article No.3576
Vorab online veröffentlicht am 08.08.2019
Nachgewiesen in Dimensions
Web of Science
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