首页|Enhancing hydrolytic stability of dynamic imine bonds and polymers in acidic media with internal protecting groups

Enhancing hydrolytic stability of dynamic imine bonds and polymers in acidic media with internal protecting groups

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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 car-boxyl 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 dy-namic covalent network and coordination supramolecular network provided a facile means for the mod-ulation 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.

Dynamic covalent chemistryInternal protecting groupKinetic stabilityImine bondDynamic polymer

Hang Chen、Chengzhi Cui、Hebo Ye、Hanxun Zou、Lei You

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College of Environmental and Biological Engineering,Fujian Provincial Key Laboratory of Ecology-Toxicological Effects & Control for Emerging Contaminants,Putian University,Putian 351100,China

State Key Laboratory of Structural Chemistry,Fujian Institute of Research on the Structure of Matter,Chinese Academy of Sciences,Fuzhou 350002,China

College of Chemistry and Material Science,Fujian Normal University,Fuzhou 350007,China

Fujian Science & Technology Innovation Laboratory for Optoelectronic Information of China,Fuzhou 350108,China

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国家自然科学基金国家自然科学基金国家自然科学基金国家自然科学基金Key Research Program of Frontier Sciences of the CAS福建省自然科学基金福建省自然科学基金Fujian Science and Technology Innovation Laboratory for Optoelectronic Information of China

22071247921560102210128322101284QYZDBSSW-SLH0302020J060352022J050852021ZR112

2024

中国化学快报(英文版)
中国化学会

中国化学快报(英文版)

CSTPCD
影响因子:0.771
ISSN:1001-8417
年,卷(期):2024.35(5)
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