FACE-selective fluorogenic cycloaddition reaction between coumarin azides and sugar terminal alkynes: an experimental and computational study

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.

Graphical abstractCopper 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.Figure optionsDownload full-size imageDownload as PowerPoint slide