中国化学快报(英文版)2024,Vol.35Issue(5) :161-165.DOI:10.1016/j.cclet.2023.109145

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

Hang Chen Chengzhi Cui Hebo Ye Hanxun Zou Lei You
中国化学快报(英文版)2024,Vol.35Issue(5) :161-165.DOI:10.1016/j.cclet.2023.109145

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

Hang Chen 1Chengzhi Cui 2Hebo Ye 3Hanxun Zou 3Lei You4
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作者信息

  • 1. College of Environmental and Biological Engineering,Fujian Provincial Key Laboratory of Ecology-Toxicological Effects & Control for Emerging Contaminants,Putian University,Putian 351100,China
  • 2. 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
  • 3. State Key Laboratory of Structural Chemistry,Fujian Institute of Research on the Structure of Matter,Chinese Academy of Sciences,Fuzhou 350002,China
  • 4. 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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Abstract

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.

Key words

Dynamic covalent chemistry/Internal protecting group/Kinetic stability/Imine bond/Dynamic polymer

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基金项目

国家自然科学基金(22071247)

国家自然科学基金(92156010)

国家自然科学基金(22101283)

国家自然科学基金(22101284)

Key Research Program of Frontier Sciences of the CAS(QYZDBSSW-SLH030)

福建省自然科学基金(2020J06035)

福建省自然科学基金(2022J05085)

Fujian Science and Technology Innovation Laboratory for Optoelectronic Information of China(2021ZR112)

出版年

2024
中国化学快报(英文版)
中国化学会

中国化学快报(英文版)

CSTPCDCSCD
影响因子:0.771
ISSN:1001-8417
参考文献量50
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