Nanographene with Multiple Embedded Heptagons: Cascade Radical Photocyclization.
Angew Chem Int Ed Engl
; 61(18): e202116955, 2022 Apr 25.
Article
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| MEDLINE
| ID: mdl-35191583
ABSTRACT
Although heptagons are widely found in graphenic materials, the precise synthesis of nanocarbons containing heptagons remains a challenge, especially for the nanocarbons containing multiple-heptagons. Herein, we show that photo-induced radical cyclization (PIRC) can be used to synthesize multi-heptagon-embedded nanocarbons. Notably, a nanographene containing six heptagons (1) was obtained via a six-fold cascade PIRC reaction. The structure of 1 was clearly validated and showed a Monkey-saddle-shaped conformation. Experimental bond analysis and theoretical calculations indicated that the heptagons in 1 were non-aromatic, whereas the peripheral rings were highly aromatic. Compared to planar nanographene with the same number of π electrons, 1 had a similar optical gap due to a compromise between the decreased conjugation in the wrapped structure and enhanced electronic delocalization at the rim. Electrochemical studies showed that 1 had low-lying oxidation potentials, which was attributed to the nitrogen-doping.
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Año:
2022
Tipo del documento:
Article
País de afiliación:
China