Citation: Jiang-Feng Xing, Kang Li, Wan Xiang, Yang-Yang Ju, Xin-Jing Zhao, Xiao-Hui Ma, Mei-Lin Zhang, Yuan-Zhi Tan. Oxa-helicenes embedding heptagons by stepwise cyclization of [6]helicene unit[J]. Chinese Chemical Letters, ;2025, 36(11): 110982. doi: 10.1016/j.cclet.2025.110982 shu

Oxa-helicenes embedding heptagons by stepwise cyclization of [6]helicene unit

State Key Laboratory for Physical Chemistry of Solid Surfaces, and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China

zhangmeilin2014@xmu.edu.cn

yuanzhi_tan@xmu.edu.cn

Received Date: 28 October 2024
Revised Date: 12 February 2025
Accepted Date: 19 February 2025
Available Online: 20 February 2025

Figures(5)

The controlled incorporation of heptagons into helicene frameworks offers a promising approach to modulate their structural and electronic properties. This study demonstrates the synthesis of two heptagon-embedded oxa-helicenes: one with a single heptagon (5) and another with two heptagons (6), achieved through controlled oxidative cyclization of a triple oxa-helicene (4). UV–vis absorption and emission spectra revealed red-shifts and slight increases in Stokes shifts from 4 to 6, attributed to π-system extension and greater structural relaxation in the excited state. 5 and 6 exhibited fluorescence quantum yields 2–3 times higher than 4. Chiral separation and thermal stability analyses showed a significant decrease in enantiomeric stability for 5 and 6 compared to 4, due to planarization effects induced by heptagon incorporation. The chiroptical properties were also investigated, revealing reduced optical dissymmetry factors after heptagon embedding.
- Oxa-helicene,
- Heptagon,
- Cyclization
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