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Self‐Assembly in Water with N‐Substituted Imines
Author(s) -
Jiao Tianyu,
Wu Guangcheng,
Zhang Yang,
Shen Libo,
Lei Ye,
Wang CaiYun,
Fahrenbach Albert C.,
Li Hao
Publication year - 2020
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.201910739
Subject(s) - imine , covalent bond , chemistry , self assembly , catenane , dynamic covalent chemistry , aqueous solution , molecule , aqueous medium , combinatorial chemistry , organic chemistry , polymer chemistry , supramolecular chemistry , catalysis
Abstract Imine synthesis has enjoyed a long history as the dynamic covalent reaction of choice for the construction of purely covalent molecular architectures. In organic solvents, the formation of imine bonds is reversible but leads to thermodynamically stable products. In the presence of water, however, imine bonds are labile, a fact which limits their utility as mediators of self‐assembly in aqueous and biological media. In this Review, we discuss water‐compatible dynamic covalent bonds based on N‐substituted imine derivatives, namely hydrazones and oximes, for the self‐assembly of metal‐free organic architectures with well‐defined structures. The reasons why hydrazones and oximes are more robust in water than their parent imines are explained. Recent progress in the self‐assembly, characterization, and design principles of a variety of complex molecules including macrocycles, cages, catenanes, and knots in aqueous media is highlighted. Emerging applications for these molecules, including guest recognition and separations, are also discussed.