Chiral self-sorting and guest recognition of porous aromatic cages

Dong-Xu Cui, Yun Geng, Jun-Ning Kou, Guo-Gang Shan, Chun-Yi Sun (), Kun-Hao Zhang, Xin-Long Wang () and Zhong-Min Su
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Dong-Xu Cui: Northeast Normal University
Yun Geng: Northeast Normal University
Jun-Ning Kou: Northeast Normal University
Guo-Gang Shan: Northeast Normal University
Chun-Yi Sun: Northeast Normal University
Kun-Hao Zhang: Chinese Academy of Sciences
Xin-Long Wang: Northeast Normal University
Zhong-Min Su: Northeast Normal University

Nature Communications, 2022, vol. 13, issue 1, 1-8

Abstract: Abstract The synthesis of ultra-stable chiral porous organic cages (POCs) and their controllable chiral self-sorting at the molecular and supramolecular level remains challening. Herein, we report the design and synthesis of a serial of axially chiral porous aromatic cages (PAC 1-S and 1-R) with high chemical stability. The theoretical and experimental studies on the chiral self-sorting reveal that the exclusive self-recognition on cage formation is an enthalpy-driven process while the chiral narcissistic and self-sorting on supramolecular assembly of racemic cages can be precisely regulated by π–π and C–H…π interactions from different solvents. Regarding the chemical stability, the crystallinity of PAC 1 is maintained in aqueous solvents, such as boiling water, high-concentrated acid and alkali; mixtures of solvents, such as 1 M H2SO4/MeOH/H2O solution, are also tolerated. Investigations on the chiral sensing performance show that PAC 1 enables enantioselective recognition of axially chiral biaryl molecules.

Date: 2022
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DOI: 10.1038/s41467-022-31785-4

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