In:
Chemistry – A European Journal, Wiley, Vol. 29, No. 32 ( 2023-06-07)
Abstract:
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.
Type of Medium:
Online Resource
ISSN:
0947-6539
,
1521-3765
DOI:
10.1002/chem.202300524
Language:
English
Publisher:
Wiley
Publication Date:
2023
detail.hit.zdb_id:
1478547-X
detail.hit.zdb_id:
1231884-X
