Aromatic Nanosandwich Obtained by σ-Dimerization of a Nanographenoid π-Radical.
Journal
Journal of the American Chemical Society
ISSN: 1520-5126
Titre abrégé: J Am Chem Soc
Pays: United States
ID NLM: 7503056
Informations de publication
Date de publication:
19 02 2020
19 02 2020
Historique:
pubmed:
31
1
2020
medline:
31
1
2020
entrez:
31
1
2020
Statut:
ppublish
Résumé
A 139-π-electron nanographenoid radical was obtained by expanding the periphery of a naphthalimide-azacoronene hybrid with a methine bridge. The radical was isolated in the form of its σ-dimer, which was shown to possess a conformationally restricted two-layer structure both in the solid state and in solution. The dimer is cleaved into its parent radicals when exposed to ultraviolet or visible radiation in toluene solutions but is resistant to thermally induced dissociation. Under inert conditions, the radicals recombine quantitatively into the σ-dimer with observable kinetics, but they are oxidized into a ketone derivative in the presence of atmospheric oxygen. Combined structural, spectroscopic, and theoretical evidence shows that the σ-dimer contains a weak C(sp
Identifiants
pubmed: 31997634
doi: 10.1021/jacs.9b13942
pmc: PMC7467677
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
3626-3635Références
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