Self‐Assembly in Water with N‐Substituted Imines

다국어 초록 (Multilingual 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.
Dynamic duo: This Review discusses novel types of water‐compatible dynamic covalent bonds for the self‐assembly of metal‐free organic molecules based on either acylhydrazone or oxime chemistry. Recent progress in the design, synthesis, and characterization in water of complex molecules with well‐defined three‐dimensional architectures, the self‐assembly of which is based on this dynamic approach, is summarized here.