期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 26, 期 53, 页码 12180-12187出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202002638
关键词
annulenes; C-F activation; collision-induced dissociation; mass spectrometry; polycyclic aromatic hydrocarbons; porphyrinoids
资金
- Deutsche Forschungsgemeinschaft (DFG) [182849149, SFB 953]
- Graduate School Molecular Science (GSMS)
- Alexander von Humboldt Foundation
- Institute for Basic Science [IBS-R026-Y1]
- Projekt DEAL
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 thefjordregion, which supports a selective pathway towards bent nitrogen-containing graphene fragments.
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