亚胺
共价键
聚合物
位阻效应
化学
反应性(心理学)
超分子聚合物
超分子化学
高分子化学
动态共价化学
组合化学
有机化学
材料科学
分子
催化作用
医学
替代医学
病理
作者
Hang Chen,C. Q. Cui,Hebo Ye,Hanxun Zou,Lei You
标识
DOI:10.1016/j.cclet.2023.109145
摘要
Imine bonds are among the most explored building motifs in dynamic chemistry, polymers, and materials, and yet, their acid-resistance remains a longstanding issue. Herein we demonstrate a concept of internal protecting groups for improving the kinetic stability of dynamic imine bonds and polymers. Systematic examination of structure-reactivity relationship of a series of aldehydes/imines bearing a neighboring carboxyl allowed uncovering of required structural features for dynamically masking imine bonds with cyclic structures. Mechanistic studies indicated that noncovalent interactions along with sterics control the ring-chain equilibrium and the stability of imine bonds. The incorporation of internal protecting groups into imine polymers further enabled their controlled stability in acidic media. Moreover, a combination of dynamic covalent network and coordination supramolecular network provided a facile means for the modulation of luminescent and mechanical properties of polymers. The strategies and results reported should be beneficial to molecular assemblies, dynamic polymers, biological delivery, and intelligent materials.
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