2022年5月2日
Protonation‐Induced Antiaromaticity in Octaaza[8]circulenes: Cyclooctatetraene Scaffolds Constrained with Four Amidine Moieties
Chemistry – An Asian Journal
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- 巻
- 17
- 号
- 12
- 開始ページ
- e202200244
- 終了ページ
- 記述言語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1002/asia.202200244
- 出版者・発行元
- Wiley
Abstract
The switching of cyclic π‐conjugation pathways using external stimuli is an attractive research topic in the field of organic chemistry. Here, we synthesized C4h‐symmetric octaaza[8]circulenes with four peripherally arranged amidine moieties that exhibit enhanced antiaromaticity upon protonation. Titration experiments with methanesulfonic acid revealed the formation of the tetraprotonated forms of the octaaza[8]circulenes in solution. Single‐crystal X‐ray diffraction analyses and theoretical calculations indicated that the contribution of the 8π antiaromatic character of the octaaza[8]circulenes is enhanced by the delocalization of charge through the protonation of the pyridine rings.
The switching of cyclic π‐conjugation pathways using external stimuli is an attractive research topic in the field of organic chemistry. Here, we synthesized C4h‐symmetric octaaza[8]circulenes with four peripherally arranged amidine moieties that exhibit enhanced antiaromaticity upon protonation. Titration experiments with methanesulfonic acid revealed the formation of the tetraprotonated forms of the octaaza[8]circulenes in solution. Single‐crystal X‐ray diffraction analyses and theoretical calculations indicated that the contribution of the 8π antiaromatic character of the octaaza[8]circulenes is enhanced by the delocalization of charge through the protonation of the pyridine rings.
- リンク情報
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- DOI
- https://doi.org/10.1002/asia.202200244
- Web of Science
- https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000789594900001&DestApp=WOS_CPL
- URL
- https://onlinelibrary.wiley.com/doi/pdf/10.1002/asia.202200244
- URL
- https://onlinelibrary.wiley.com/doi/full-xml/10.1002/asia.202200244
- ID情報
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- DOI : 10.1002/asia.202200244
- ISSN : 1861-4728
- eISSN : 1861-471X
- ORCIDのPut Code : 113747025
- Web of Science ID : WOS:000789594900001