Citation: Heng Qiu, Wang Xie, Mingxia Ye, Conghao Shi, Juli Jiang, Zhouyu Wang, Wim Dehaen, Leyong Wang. Reaction-driven crystallization: Gram-scale synthesis of chiral macrocycles bearing Tröger's base with self-sorting[J]. Chinese Chemical Letters, ;2026, 37(7): 111966. doi: 10.1016/j.cclet.2025.111966 shu

Reaction-driven crystallization: Gram-scale synthesis of chiral macrocycles bearing Tröger's base with self-sorting

Heng Qiu ^a ,
Wang Xie ^a ,
Mingxia Ye ^a ,
Conghao Shi ^a ,
Juli Jiang ^a ,
Zhouyu Wang ^b ,
Wim Dehaen ^{c, *,} ,
Leyong Wang ^{a, b, *,}

a.
State Key Laboratory of Analytical Chemistry for Life Science, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China
b.
Sichuan Engineering Research Center for Molecular Targeted Diagnostic & Therapeutic Drugs, Department of Chemistry, Xihua University, Chengdu 610039, China
c.
Department of Chemistry, KU Leuven, 3001 Leuven, Belgium

wim.dehaen@kuleuven.be

lywang@nju.edu.cn

Received Date: 3 July 2025
Revised Date: 30 September 2025
Accepted Date: 14 October 2025
Available Online: 15 October 2025

Figures(7)

Efficient macrocycle synthesis remains a persistently pursued objective in supramolecular chemistry. In this work, a series of chiral macrocycles (TBCHMs) incorporating Tröger's base were synthesized via imine condensation reactions from Tröger's base (TB) aldehyde derivatives and cyclohexane-1,2-diamines (CHDA). Gram-scale quantities of crystalline macrocycles were directly obtained during the process of their reaction. Precise modulation of macrocycle structural morphology was achieved by varying the chiral configuration of the components. Notably, chiral self-sorting was realized in these reaction systems, driven by the energy difference between diastereomers and their selective precipitation as crystals. This work might open up new insights for the modular preparation of chiral macrocycles based on dynamic covalent chemistry (DCC).
- TB-based macrocycles,
- Gram-scale synthesis,
- Crystallization assembly,
- Chiral self-sorting,
- Dynamic covalent chemistry
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