FACE-selective fluorogenic cycloaddition reaction between coumarin azides and sugar terminal alkynes: an experimental and computational study |
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| Authors: | Rajaganesh Ramanathan Ravinder Pawar Subramanian Venkatesan Mohan Das Thangamuthu |
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| Affiliation: | aDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India;bChemical Laboratory, Central Leather Research Institute (CSIR), Adyar, Chennai 600 025, India |
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| Abstract: | Copper catalyzed azide–alkyne cycloaddition reaction (CuAAC) of non-fluorescent coumarin azides and sugar terminal alkynes afforded intense fluorescent 1,2,3-triazoles in 75–85% of yield. The photophysical properties of coumarin–sugar triazoles influenced greatly, upon introducing different substituents at 6th and 7th positions. The experimental observations were further supported by TD-DFT computational studies. |
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| Keywords: | Protected sugars O-Glycosides Coumarin Triazole Click chemistry Fluorescence |
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