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.