Molecular Cages Self‐Assembled by Imine Condensation in Water

Self‐assembly by imine condensation in aqueous media is a formidable task because of the labile nature of imines in the presence of water. Here, by taking advantage of multivalence and ligand preorganization, basket‐shaped triscationic cage molecules are self‐assembled in high yields in both water a...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2021-02, Vol.60 (9), p.4705-4711
Main Authors: Lei, Ye, Chen, Qiong, Liu, Peiren, Wang, Lingxiang, Wang, Hongye, Li, Bingda, Lu, Xingyu, Chen, Zhong, Pan, Yuanjiang, Huang, Feihe, Li, Hao
Format: Article
Language:English
Subjects:
Aldehydes
Amines
Aqueous solutions
Assembly
Cage molecules
Chemical precipitation
Condensation
Dilution
dynamic covalent chemistry
Enantiomers
host-guest chemistry
Hydrophobicity
Imines
molecular recognition
self-assembly
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Summary:Self‐assembly by imine condensation in aqueous media is a formidable task because of the labile nature of imines in the presence of water. Here, by taking advantage of multivalence and ligand preorganization, basket‐shaped triscationic cage molecules are self‐assembled in high yields in both water and organic solvent, by condensing a hexaformyl and bisamine. These cages, especially the chiral ones, are stable or inert in aqueous solution, that is, no decomposition was observed upon dilution, precipitation, or exposure to competitive amines or aldehydes. Such water‐compatibility allows the hosts to take advantage of the hydrophobic effect to accommodate hydrophobic guests. The chiral cage S‐23+ selectively binds and distinguishes one of two enantiomers, opening up opportunities for applications such as chiral compound separation. Chiral narcissistic self‐sorting and sergeants‐and‐soldiers effects occur during cage formation when two amino precursors are involved in self‐assembly. By taking advantage of multivalence and ligand preorganization, a series of basket‐shaped cages are self‐assembled by imine condensation in water. These cages are rather stable and inert against hydrolysis, and therefore they are able to take advantage of the hydrophobic effect for guest recognition.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202013045