Citation: Hao Zhou, Xu-Dong Wang, Yu-Fei Ao, De-Xian Wang, Qi-Qiang Wang. Inherently chiral molecular barrels via directional cascade hooping[J]. Chinese Chemical Letters, ;2026, 37(5): 111443. doi: 10.1016/j.cclet.2025.111443 shu

Inherently chiral molecular barrels via directional cascade hooping

Hao Zhou ^{a, b} ,
Xu-Dong Wang ^a ,
Yu-Fei Ao ^{a, b} ,
De-Xian Wang ^{a, b} ,
Qi-Qiang Wang ^{a, b, *,}

a.
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
b.
University of Chinese Academy of Sciences, Beijing 100049, China

qiqiangw@iccas.ac.cn

Received Date: 30 March 2025
Revised Date: 27 May 2025
Accepted Date: 10 June 2025
Available Online: 11 June 2025

Figures(5)

A kind of inherently chiral molecular barrels were efficiently constructed by a directional cascade hooping strategy. This strategy involves the anchoring of three nonsymmetric connecting arms onto a cap-dissymmetric bis(tetraoxacalix[2]arene[2]triazine) cage core, followed by hooping via imine condensation and reduction to afford the target molecular barrels with well-defined connectivity. The precise and high-yielding synthesis stems from both the bidirectional C_triazine-N bond flipping dynamics and the reversible nature of imine formation. The molecular barrels comprise a bis(tetraoxacalix[2]arene[2]triazine) core encircled by a 72-membered loop, forming three fan-shaped cavities with inherent chirality and multiple endo-functionalized sites. The existence of multiple diastereoisomeric conformers due to the restricted C_triazine-N bond flipping by the constrained loop structure was revealed by variable-temperature NMR studies and DFT calculations.
- Inherent chirality,
- Molecular cage,
- Desymmetrization,
- Imine condensation,
- Conformation interconversion
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