Organic Letters
Organic Letters
5 years ago

Synthesis, Structure, and Properties of Tetrabenzo[7]circulene

Synthesis, Structure, and Properties of Tetrabenzo[7]circulene
Bowen Shan, Huiyan Li, Qian Miao, Zhifeng Liu, Xiao Gu
Tetrabenzo[7]circulene, a new member of aromatic saddles, was conveniently synthesized from 2-(1-naphthoyl)benzoic acid with the seven-membered ring constructed at an early stage of the synthesis. This method, upon minor modification, was also useful for synthesis of thiophene-annulated [7]circulenes. The structures of tetrabenzo[7]circulene and [7]circulene were compared in terms of symmetry, flexibility, and curvature on the basis of DFT calculations and X-ray crystallography. It was also found that tetrabenzo[7]circulene functioned as a p-type semiconductor in thin-film transistors and cocrystallized with C60.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00714

DOI: 10.1021/acs.orglett.7b00714

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