Photophysical characterization of triazole-substituted coumarin fluorophores |
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| Authors: | Jessie A Key Sherni Koh Qadir K Timerghazin Alex Brown Christopher W Cairo |
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| Affiliation: | 1. Alberta Ingenuity Centre for Carbohydrate Science, Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada;2. Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada;1. Department of Physics, B.N.M. Institute of Technology, Bangalore 560 070, India;2. Department of Physics, Bangalore Institute of Technology, Bangalore 560 004, India;3. P.G. Department of Studies in Chemistry, K.L.E. Society’s P.C. Jabin Science College, Hubli 580 031, India;1. Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry and Materials Science, Northwest University, Xi''an, 710127, PR China;2. College of Chemistry and Chemical Engineering, Xi''an Shiyou University, Xi''an, 710065, PR China;1. Key Laboratory of Opto-Electronic Technology and Intelligent Control (Ministry of Education), Lanzhou Jiaotong University, Lanzhou 730070, China;2. School of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, China;3. School of Mechatronic Engineering, Lanzhou Jiaotong University, Lanzhou 730070, China |
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| Abstract: | 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 (TD 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. |
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