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Three-dimensional aromaticity in an antiaromatic cyclophane

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...

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Autores principales: Nozawa, Ryo, Kim, Jinseok, Oh, Juwon, Lamping, Anna, Wang, Yemei, Shimizu, Soji, Hisaki, Ichiro, Kowalczyk, Tim, Fliegl, Heike, Kim, Dongho, Shinokubo, Hiroshi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6687811/
https://www.ncbi.nlm.nih.gov/pubmed/31395873
http://dx.doi.org/10.1038/s41467-019-11467-4
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author Nozawa, Ryo
Kim, Jinseok
Oh, Juwon
Lamping, Anna
Wang, Yemei
Shimizu, Soji
Hisaki, Ichiro
Kowalczyk, Tim
Fliegl, Heike
Kim, Dongho
Shinokubo, Hiroshi
author_facet Nozawa, Ryo
Kim, Jinseok
Oh, Juwon
Lamping, Anna
Wang, Yemei
Shimizu, Soji
Hisaki, Ichiro
Kowalczyk, Tim
Fliegl, Heike
Kim, Dongho
Shinokubo, Hiroshi
author_sort Nozawa, Ryo
collection PubMed
description 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.
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spelling pubmed-66878112019-08-12 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 Nat Commun Article 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. Nature Publishing Group UK 2019-08-08 /pmc/articles/PMC6687811/ /pubmed/31395873 http://dx.doi.org/10.1038/s41467-019-11467-4 Text en © The Author(s) 2019 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
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
title Three-dimensional aromaticity in an antiaromatic cyclophane
title_full Three-dimensional aromaticity in an antiaromatic cyclophane
title_fullStr Three-dimensional aromaticity in an antiaromatic cyclophane
title_full_unstemmed Three-dimensional aromaticity in an antiaromatic cyclophane
title_short Three-dimensional aromaticity in an antiaromatic cyclophane
title_sort three-dimensional aromaticity in an antiaromatic cyclophane
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6687811/
https://www.ncbi.nlm.nih.gov/pubmed/31395873
http://dx.doi.org/10.1038/s41467-019-11467-4
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