Citation: Hang Chen, Chengzhi Cui, Hebo Ye, Hanxun Zou, Lei You. Enhancing hydrolytic stability of dynamic imine bonds and polymers in acidic media with internal protecting groups[J]. Chinese Chemical Letters, ;2024, 35(5): 109145. doi: 10.1016/j.cclet.2023.109145 shu

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

Hang Chen ^{b, 1} ,
Chengzhi Cui ^{a, c, 1} ,
Hebo Ye ^{a, *,} ,
Hanxun Zou ^a ,
Lei You ^{a, c, d, *,}

a.
State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, China
b.
College of Environmental and Biological Engineering, Fujian Provincial Key Laboratory of Ecology-Toxicological Effects & Control for Emerging Contaminants, Putian University, Putian 351100, China
c.
College of Chemistry and Material Science, Fujian Normal University, Fuzhou 350007, China
d.
Fujian Science & Technology Innovation Laboratory for Optoelectronic Information of China, Fuzhou 350108, China

yehebo@fjirsm.ac.cn

lyou@fjirsm.ac.cn

Received Date: 29 May 2023
Revised Date: 8 September 2023
Accepted Date: 21 September 2023
Available Online: 24 September 2023

Figures(4)

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.
- Dynamic covalent chemistry,
- Internal protecting group,
- Kinetic stability,
- Imine bond,
- Dynamic polymer
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