Gas-Phase Transformation of Fluorinated Benzoporphyrins to Porphyrin-Embedded Conical Nanocarbons.
C−F activation
annulenes
collision-induced dissociation
mass spectrometry
polycyclic aromatic hydrocarbons
porphyrinoids
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
21 Sep 2020
21 Sep 2020
Historique:
received:
31
05
2020
pubmed:
25
6
2020
medline:
25
6
2020
entrez:
25
6
2020
Statut:
ppublish
Résumé
Geodesic nitrogen-containing graphene fragments are interesting candidates for various material applications, but the available synthetic protocols, which need to overcome intrinsic strain energy during the formation of the bowl-shaped skeletons, are often incompatible with heteroatom-embedded structures. Through this mass spectrometry-based gas-phase study, we show by means of collision-induced dissociation experiments and supported by density functional theory calculations, the first evidence for the formation of a porphyrin-embedded conical nanocarbon. The influences of metalation and functionalization of the used tetrabenzoporphyrins have been investigated, which revealed different cyclization efficiencies, different ionization possibilities, and a variation of the dissociation pathway. Our results suggest a stepwise process for HF elimination from the fjord region, which supports a selective pathway towards bent nitrogen-containing graphene fragments.
Identifiants
pubmed: 32578918
doi: 10.1002/chem.202002638
pmc: PMC7540561
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
12180-12187Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : 182849149
Organisme : Institute for Basic Science
ID : IBS-R026-Y1
Informations de copyright
© 2020 The Authors. Published by Wiley-VCH GmbH.
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