Dewar Benzenoids Discovered in Carbon Nanobelts

Hanson-Heine, Magnus W.D.; Rogers, David M.; Woodward, Simon; Hirst, Jonathan D.

Abstract

© 2020 American Chemical Society. The synthesis of cyclacene nanobelts remains an elusive goal dating back over 60 years. These molecules represent the last unsynthesized building block of carbon nanotubes and may be useful both as seed molecules for the preparation of structurally well-defined carbon nanotubes and for understanding the behavior and formation of zigzag nanotubes more broadly. Here we report the discovery that isomers containing two Dewar benzenoid rings are the preferred form for several sizes of cyclacene. The predicted lower polyradical character and higher singlet-triplet stability that these isomers possess compared with their pure benzenoid counterparts suggest that they may be more stable synthetic targets than the structures that have previously been identified. Our findings should facilitate the exploration of new routes to cyclacene synthesis through Dewar benzene chemistry.

Citation

Hanson-Heine, M. W., Rogers, D. M., Woodward, S., & Hirst, J. D. (2020). Dewar Benzenoids Discovered in Carbon Nanobelts. Journal of Physical Chemistry Letters, 11(10), 3769-3772. https://doi.org/10.1021/acs.jpclett.0c01027

• Journal Article Type: Article
• Acceptance Date: Apr 22, 2020
• Online Publication Date: Apr 22, 2020
• Publication Date: May 21, 2020
• Deposit Date: Apr 27, 2020
• Publicly Available Date: Apr 23, 2021
• Journal: Journal of Physical Chemistry Letters
• Print ISSN: 1948-7185
• Electronic ISSN: 1948-7185
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 11
• Issue: 10
• Pages: 3769-3772
• DOI: https://doi.org/10.1021/acs.jpclett.0c01027
• Public URL: https://nottingham-repository.worktribe.com/output/4349213
• Publisher URL: https://pubs.acs.org/doi/10.1021/acs.jpclett.0c01027
• Additional Information: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Physical Chemistry Letters, copyright©American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.jpclett.0c01027