Citation: Wenxiong Yu, Chenyu Yang, Xian Feng, Chengshuo Shen. Scholl cyclization of [6]helicenes into negatively curved hexa[7]circulenes[J]. Chinese Chemical Letters, ;2025, 36(11): 110939. doi: 10.1016/j.cclet.2025.110939 shu

Scholl cyclization of [6]helicenes into negatively curved hexa[7]circulenes

Wenxiong Yu ^a ,
Chenyu Yang ^b ,
Xian Feng ^a ,
Chengshuo Shen ^{a, c, *,}

a.
School of Chemistry and Chemical Engineering, Zhejiang Sci-Tech University, Hangzhou 310000, China
b.
School of Chemistry and Chemical Engineering, Zhangjiang Institute for Advanced Study, Frontiers Science Center for Transformative Molecules, State Key Laboratory of Metal Matrix Composites, Shanghai Jiao Tong University, Shanghai 200240, China
c.
Zhejiang Sci-Tech University Shengzhou Innovation Research Institute, Shengzhou 312400, China

shenchengshuo@zstu.edu.cn

Received Date: 27 September 2024
Revised Date: 25 January 2025
Accepted Date: 9 February 2025
Available Online: 10 February 2025

Figures(7)

The Scholl cyclization for creating seven-membered rings is of great importance in synthesizing negatively curved polycyclic aromatic compounds. In this study, we systematically report a methodical approach for converting [6]helicenes into negatively curved hexa[7]circulene using Scholl cyclization. The reaction revealed that the electron-donating substituents on the helicene terminal rings of helicenes facilitate the cyclization process while electron-withdrawing substituents would impede the cyclization. This was supported by theoretical calculations on the reaction process focusing on the arenium cation pathways. Through the application of this Scholl cyclization, a series of negatively curved hexa[7]circulene derivatives were synthesized, showing highly curved and twisted geometries. Notably, 2,15-substituted derivatives exhibited high conformational stability against racemization, thereby performing circularly polarized luminescence with |g_lum| up to 4 × 10⁻³.
- Scholl reaction,
- Helicene,
- Circulene,
- Negative curvature,
- Chirality
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沈阳化工大学材料科学与工程学院沈阳 110142