title: FACE-selective fluorogenic cycloaddition reaction between coumarin azides and sugar terminal alkynes: an experimental and computational study.
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.
authors.affiliation: Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India.
authors.forename: Ramanathan
authors.initials: R
authors.lastname: Rajaganesh
authors.forename: Pawar
authors.initials: P
authors.lastname: Ravinder
authors.forename: Venkatesan
authors.initials: V
authors.lastname: Subramanian
authors.forename: Thangamuthu
authors.initials: T
authors.lastname: Mohan Das
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003198:Computer Simulation; D003300:Copper / Q000737:chemistry; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006868:Hydrolysis; D008958:Models, Molecular; D013053:Spectrophotometry
chemical_list: D000480:Alkynes; D001386:Azides; D003374:Coumarins; D006027:Glycosides; D003300:Copper