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Protonation‐Induced Antiaromaticity in Octaaza[8]circulenes: Cyclooctatetraene Scaffolds Constrained with Four Amidine Moieties.
- Source :
-
Chemistry - An Asian Journal . Jun2022, Vol. 17 Issue 12, p1-8. 8p. - Publication Year :
- 2022
-
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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 18614728
- Volume :
- 17
- Issue :
- 12
- Database :
- Academic Search Index
- Journal :
- Chemistry - An Asian Journal
- Publication Type :
- Academic Journal
- Accession number :
- 157461890
- Full Text :
- https://doi.org/10.1002/asia.202200244