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- Title
Revisiting the Octadehydro[12]annulenes.
- Authors
Holland, Emma K.; Thorley, Karl J.; Parkin, Sean R.; Anthony, John E.
- Abstract
Dehydroannulenes are alkyne‐rich macrocycles possessing rigid, planar, π‐conjugated backbones. Octadehydro[12]annulenes in particular are formally antiaromatic, and have been shown to possess stable reduced states with exploitable LUMO energies. However, very few examples of this type of annulene have been structurally characterized, and there is little information on the stability of these antiaromatic molecules in solution or in the solid state. We have synthesized a range of substituted octadehydro[12]annulenes, and characterized their optical and redox properties. Contrary to prior reports, dehydro[12]annulenes with overlapping π‐surfaces are reasonably stable both in solution and thin films, suggesting potential use in practical applications.
- Subjects
ANNULENES; SOLID solutions; THIN films; OPTICAL properties
- Publication
European Journal of Organic Chemistry, 2021, Vol 2021, Issue 44, p5934
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202101067