期刊
DYES AND PIGMENTS
卷 82, 期 2, 页码 196-203出版社
ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2009.01.001
关键词
Fluorescent dye; Triazole; Coumarin; Click chemistry; Absorbance; Fluorescence; Bioconjugate
资金
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Alberta Ingenuity Centre for Carbohydrate Science (AICCS)
- University of Alberta
- University of Alberta Spectral Services
- Canadian Foundation for Innovation
The photophysical properties of fluorochromes are directly influenced by their chemical structure. There is increasing interest in chemical strategies that provide controlled changes to the emission properties of biologically compatible fluorophores. One strategy employed is the conversion of a fluorophore-attached alkyne to a triazole through a copper-catalyzed Sharpless-Meldal reaction. In this study, we have examined a series of structurally related coumarin fluorophores and evaluated changes in their photophysical properties upon conversion from alkyne to triazole forms. Ethynyl-coumarin structures showed increases in quantum yield (ca. 1.2- to- 9 fold) and bathochromic shifts (up to 23 nm) after triazole formation. To extend these results, we tested the ability of time-dependent density functional theory (TO DFT) to predict the observed changes in fluorophore absorption properties. We found excellent correlation between the predicted absorption values and experiment, providing a useful tool in the design of new fluorogenic probes. (C) 2009 Elsevier Ltd. All rights reserved.
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