Water-stable boroxine structure with dynamic covalent bonds

Xiaopei Li, Yongjie Zhang, Zhenqiang Shi, Dongdong Wang, Hang Yang, Yahui Zhang, Haijuan Qin, Wenqi Lu, Junjun Chen, Yan Li and Guangyan Qing ()
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Xiaopei Li: CAS Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences
Yongjie Zhang: Dalian Polytechnic University
Zhenqiang Shi: CAS Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences
Dongdong Wang: CAS Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences
Hang Yang: CAS Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences
Yahui Zhang: CAS Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences
Haijuan Qin: Tianjin University of Science & Technology
Wenqi Lu: CAS Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences
Junjun Chen: CAS Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences
Yan Li: CAS Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences
Guangyan Qing: CAS Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences

Nature Communications, 2024, vol. 15, issue 1, 1-12

Abstract: Abstract Boroxines are significant structures in the production of covalent organic frameworks, anion receptors, self-healing materials, and others. However, their utilization in aqueous media is a formidable task due to hydrolytic instability. Here we report a water-stable boroxine structure discovered from 2-hydroxyphenylboronic acid. We find that, under ambient environments, 2-hydroxyphenylboronic acid undergoes spontaneous dehydration to form a dimer with dynamic covalent bonds and aggregation-induced enhanced emission activity. Intriguingly, upon exposure to water, the dimer rapidly transforms into a boroxine structure with excellent pH stability and water-compatible dynamic covalent bonds. Building upon these discoveries, we report the strong binding capacity of boroxines toward fluoride ions in aqueous media, and develop a boroxine-based hydrogel with high acid–base stability and reversible gel–sol transition. This discovery of the water-stable boroxine structure breaks the constraint of boroxines not being applicable in aqueous environments, opening a new era of researches in boroxine chemistry.

Date: 2024
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DOI: 10.1038/s41467-024-45464-z

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