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Review
. 2019 Nov 18;58(47):16966-16972.
doi: 10.1002/anie.201907972. Epub 2019 Oct 7.

A Nitrogen-Doped Hexapole [7]Helicene versus Its All-Carbon Analogue

Xiaoyu Guo  1 , Ziyong Yuan  1 , Yanpeng Zhu  1 , Zhihao Li  1 , Ruikang Huang  1 , Zeming Xia  1 , Weixiong Zhang  1 , Yang Li  2 , Jiaobing Wang  1
Affiliations
Review

A Nitrogen-Doped Hexapole [7]Helicene versus Its All-Carbon Analogue

Xiaoyu Guo et al. Angew Chem Int Ed Engl. .

Abstract

Two synthetic nanographenes (NGs), N-H7H and C-H7H, were prepared. N-H7H is doped with nitrogen, and C-H7H is the all-carbon analogue. Both are hexapole [7]helicenes (H7Hs), and their structures were identified by single-crystal X-ray diffraction. Sharp contrasts in absorption (abs λmax , 683 vs. 593 nm), emission (em λmax , 894 vs. 777 nm), and electrochemical behavior (ox E1 , 0.28 vs. 0.53 V) were observed between N-H7H and C-H7H, and the origin of these differences was rationalized by theoretical calculations. Studies on N-H7H and C-H7H set a clear example to elucidate the remarkable effects of N-doping on the physical properties of NGs.

Keywords: electronic structure; helical structures; heteroarenes; heteroatom doping; nanographenes.

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