Molecular Cages Self‐Assembled by Imine Condensation in Water. (12th January 2021)

• Record Type: Journal Article
• Authors: Lei, Ye; Chen, Qiong; Liu, Peiren; Wang, Lingxiang; Wang, Hongye; Li, Bingda; Lu, Xingyu; Chen, Zhong; Pan, Yuanjiang; Huang, Feihe; Li, Hao
• Is Part Of: Angewandte Chemie. Volume 133:Number 9(2021)
• Page Start: 4755
• Page End: 4761
• Publication Date: 2021-01-12
• Subjects: dynamic covalent chemistry -- host-guest chemistry -- imines -- molecular recognition -- self-assembly; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202013045
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: 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 ‐2 3+ 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. Abstract : 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.