Synthesis of 2,5-diaryl-4-halo-1,2,3-triazoles and comparative study of their fluorescent properties |
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| Authors: | Vladimir A. Motornov Andrey A. Tabolin Roman A. Novikov Nikolay E. Shepel Valentine G. Nenajdenko Sema L. Ioffe |
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| Affiliation: | 1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow, 119991, Russia;2. Higher Chemical College, D. I. Mendeleev University of Chemical Technology of Russia, Miusskaya sq. 9, Moscow, 125047, Russia;3. V. A. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilov str. 32, Moscow, 119991, Russia;4. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, Moscow, 119991, Russia;5. Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskiye Gory 1, Moscow, 119991, Russia |
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| Abstract: | A convenient method for arylation of mono- and disubstituted 1,2,3-triazoles by copper-catalyzed Chan-Lam coupling was developed. The method is applicable for the regioselective synthesis of fluorescent 4-halogen-substituted (Hal?=?F, Cl, Br) 2,5-diaryl-1,2,3-triazoles in high yields. Comparative study of their fluorescent properties revealed that 4-fluorosubstituted triazoles possess the highest quantum yield (up to 0.69) among halogenated triazoles possessing Cl and Br in the position 4. |
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| Keywords: | 1,2,3-Triazoles Chan-Lam coupling Organofluorine compounds Near UV luminescence Copper catalysis |
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