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Dewar Benzenoids Discovered in Carbon Nanobelts

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

Authors

SIMON WOODWARD simon.woodward@nottingham.ac.uk
Professor of Synthetic Organic Chemistry



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