期刊
NEW JOURNAL OF CHEMISTRY
卷 37, 期 5, 页码 1554-1560出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3nj00193h
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资金
- 973 Program [2011CB932502]
- NNSFC [20932004, 21102075]
- Fundamental Research Funds for the Central Universities
- Specialized Research Fund for the Doctoral Program of Higher Education [20110031120014]
Three bridged bis(beta-cyclodextrin)s 3-5 possessing 1,2,3-triazole moieties and polyether chains of different lengths have been synthesized by click reactions in high yields. Their binding affinities towards four cinchona alkaloids, namely, cinchonine, cinchonidine, quinine, and quinidine, have been quantitatively investigated by means of spectrophotometric titrations and 2D NMR spectroscopy. Spectroscopic analyses demonstrated that, compared with native beta- and gamma-cyclodextrins, bridged bis(beta-cyclodextrin)s with a rigid spacer give enhanced molecular binding abilities towards the selected substrates. Moreover, the factors resulting in the significant differences in photophysical behaviors of bridged bis(beta-cyclodextrin)s towards cinchona alkaloids are discussed from the viewpoint of the binding geometry of host-guest complexes, revealing that the aromatic ring containing the nitrogen atom of quinine is accommodated in the cavity of 3, whereas the rings of cinchonine, cinchonidine, and quinidine are located out of the cavity of the cyclodextrin and are exposed to aqueous media.
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