Abstract
We developed a pyridine–acetylene–phenol macrocycle in which a fluorine atom was introduced in place of a hydroxy group, as a host for the selective binding to epimers of glucose. The fluorine atom was expected to work as a negatively charged infill repelling oxygen atoms of saccharides and prevent the efficient formation of a hydrogen-bond network with a glucoside, whose cross-section size is larger than those of the corresponding epimers, especially of a mannoside. UV–Vis and fluorescence titration experiments revealed that this host showed a higher affinity for a mannoside than a glucoside. 1H NMR and molecular modeling suggested that the fluorine atom acts as a moderate infill weakening the binding to a glucoside. This result indicates that selectivity for guest molecules can be modified by replacing a hydroxy group and a hydrogen atom in host molecules with a fluorine atom.
Original language | English |
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Article number | e202400758 |
Journal | European Journal of Organic Chemistry |
Volume | 27 |
Issue number | 45 |
DOIs | |
State | Published - 2024/12/02 |
Keywords
- Fluorine
- Hydrogen bonds
- Macrocycles
- Molecular recognition
- Saccharides
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry