title: Construction of triazolyl bidentate glycoligands (TBGs) by grafting of 3-azidocoumarin to epimeric pyranoglycosides via a fluorogenic dual click reaction.
abstract: Glycoligands, which feature a glycoside as the central template incorporating Lewis bases as metal chelation sites and various fluorophores as the chemical reporter, represent a range of interesting scaffolds for development of chemosensors. Here, new types of triazolyl bidentate glycoligands (TBGs) based on the grafting of 3-azidocoumarin to the C2,3- or C4,6-positions of three epimeric pyranoglycosides including a glucoside, a galactoside, and a mannoside were efficiently synthesized via a fluorogenic dual click reaction assisted by microwave irradiation. The desired TBGs were afforded in high conversion rates (>90%) and reasonable yields (∼70%). Moreover, a preliminary optical study of two hydroxyl-free glucoside-based TBGs indicates that these compounds are strongly fluorescent in pure water, implying their potential for ion detections in aqueous media.
authors.affiliation: Key Laboratory for Advanced Materials & Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237, PR China.
authors.forename: Jia-Lu
authors.initials: JL
authors.lastname: Xue
authors.forename: Xiao-Peng
authors.initials: XP
authors.lastname: He
authors.forename: Jin-Wei
authors.initials: JW
authors.lastname: Yang
authors.forename: De-Tai
authors.initials: DT
authors.lastname: Shi
authors.forename: Chao-Ying
authors.initials: CY
authors.lastname: Cheng
authors.forename: Juan
authors.initials: J
authors.lastname: Xie
authors.forename: Guo-Rong
authors.initials: GR
authors.lastname: Chen
authors.forename: Kaixian
authors.initials: K
authors.lastname: Chen
mesh_terms: D001386:Azides / Q000737:chemistry*; D057930:Click Chemistry; D003374:Coumarins / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D008024:Ligands; D013237:Stereoisomerism; D014230:Triazoles / Q000737:chemistry*
chemical_list: C507184:3-azido-7-hydroxycoumarin; D001386:Azides; D003374:Coumarins; D005456:Fluorescent Dyes; D006027:Glycosides; D008024:Ligands; D014230:Triazoles