Premium
Molecular Cages Self‐Assembled by Imine Condensation in Water
Author(s) -
Lei Ye,
Chen Qiong,
Liu Peiren,
Wang Lingxiang,
Wang Hongye,
Li Bingda,
Lu Xingyu,
Chen Zhong,
Pan Yuanjiang,
Huang Feihe,
Li Hao
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202013045
Subject(s) - imine , chemistry , aqueous solution , cage , condensation , solvent , self assembly , molecule , condensation reaction , organic chemistry , catalysis , physics , mathematics , combinatorics , thermodynamics
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.