1. A water-soluble aza-adamantyl nitroxide radical and its complexes with β-cyclodextrin derivatives.
- Author
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Zhao, Yani, Duan, Ran, Guo, Weijie, Lyu, Lele, Liu, Xiaoyu, Jiang, Hua, and Wang, Ying
- Subjects
NITROXIDES ,CYCLODEXTRIN derivatives ,CYCLODEXTRINS ,INCLUSION compounds ,POLAR effects (Chemistry) ,ELECTRONIC structure ,WATER temperature ,SOLUBILITY - Abstract
We describe the synthesis and characterization of a hydroxylated aza-adamantyl nitroxide radical Z-3, with the solubility in water of 170 mM at room temperature. We find that hydroxylation has no significant effect on the electronic structure and stability of aza-adamantyl nitroxides. We prepare a series of β-cyclodextrin (β-CD) derivatives which can form stoichiometric 1 : 1 inclusion complexes with Z-3, to investigate their effects on water solubility and stability of the radical upon complexation. The results indicate that water solubility of Z-3 increases by 1.4–3 times, while the radical stability somewhat decreases, depending on different β-CD substituents. Overall, sodium disulfobutylether-β-CD shows the best result in complexation with Z-3, providing water solubility >0.35 mol L
−1 , while maintaining the stability of the nitroxide radical with a half-life of 13.5 days at room temperature in water. [ABSTRACT FROM AUTHOR]- Published
- 2024
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