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Synthesis of a Sidewall Fragment of a (12,0) Carbon Nanotube
Author(s) -
Han Yi,
Dong Shaoqiang,
Shao Jiawei,
Fan Wei,
Chi Chunyan
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202012651
Subject(s) - zigzag , aromatization , carbon nanotube , graphene , aromaticity , conjugated system , electronic structure , nanotube , carbon fibers , materials science , chemistry , nanotechnology , molecule , crystallography , computational chemistry , organic chemistry , polymer , catalysis , composite material , geometry , mathematics , composite number
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 . 1 H 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.