氢键
化学
共价键
亚胺
酰胺
吡啶
组合化学
分子识别
有机化学
立体化学
分子
催化作用
作者
Canjia Zhai,Chenyang Xu,Yunpeng Cui,Łukasz Wojtas,Wenqi Liu
标识
DOI:10.1002/chem.202300524
摘要
A biomimetic receptor for glucose has been developed with high affinity and selectivity. The receptor was efficiently synthesized in three steps through dynamic imine chemistry followed by imine-to-amide oxidation. The receptor features two parallel durene panels, forming a hydrophobic pocket for [CH⋅⋅⋅π] interactions, and two pyridinium residues directing four amide bonds towards the pocket. These pyridinium residues not only improve solubility but also provide polarized C-H bonds for hydrogen bonding. Experimental data and DFT calculations show that these polarized C-H bonds significantly enhance substrate binding. These findings demonstrate the power of dynamic covalent chemistry for creating molecular receptors and using polarized C-H bonds for boosted carbohydrate recognition in water, providing a foundation for developing glucose-responsive materials and sensors.
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