期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 5, 页码 2658-2662出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202012651
关键词
carbon nanobelts; deoxgenative aromatization; single-walled carbon nanotubes; strain; zigzag edge
资金
- MOE [R-143-000-B62-114, MOE2018-T2-1-152]
The successful synthesis of a carbon nanobelt (CNB) and the characterization of its unique structure and properties were reported in this study. The findings provide a new strategy for the synthesis of highly strained CNBs.
Synthesis of a carbon nanobelt (CNB) is a very challenging task in organic chemistry. Herein, we report the successful synthesis of an octabenzo[12]cyclacene based CNB (6), which can be regarded as a sidewall fragment of a (12,0) carbon nanotube. The key intermediate compound, a tetraepoxy nanobelt (5), was first synthesized by Diels-Alder reaction, and subsequent reductive aromatization gave the fully conjugated CNB 6. X-ray crystallographic analysis unambiguously confirmed the belt-shaped structure of 6. H-1 NMR spectrum and theoretical calculations (ACID, NICS, and 2D/3D ICSS) revealed localized aromaticity and stronger shielding chemical environment in the inner region of the belt. The optical properties (absorption and emission) of 6 were studied and correlated to its electronic structure. Strain analysis indicates that the phenyl substituents at the zigzag edges are crucial to the successful synthesis of 6. This report presents a new strategy towards highly strained CNBs.
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