Optical and electrochemical dual channel sensing of Cu2+ using functionalized furo[2,3-d]pyrimidines-2,4[1H,3H]-diones

Abstract

Owing to their easy accessibility and high degree of structural and functional diversity, many multicomponent reactions (MCRs) have been a rich source of conjugate π-systems, functionalised chromophores (or fluorophore) and redox active molecules. Despite their high explorative potential and practical benefits, only a few MCR products have been so far investigated for their metal sensing abilities. In the present report, two furopyrimidinones (FPys) based molecular systems have been synthesized by [4+1] cycloaddition based MCR sequence. Designed chemosensors displayed optic (absorption spectra) as well as electroanalytical (ion selective electrode) response toward Cu ion in solution and membrane phase respectively (dual channel sensing). Different aspects of both the sensing phenomena such as selectivity, association constants, detection limit, membrane composition etc. were studied in detail using UV-Vis spectroscopy, NMR titration and cell assembly. Both the compounds showed excellent performance characteristics such as high selectivity, acceptable affinity and low detection limits (10M) in both sensing assays with potential utility in the area of sample monitoring.

Synthesis of Phenol-Hydrazide-Appended Tetraphenylethenes as Novel On–Off–On Cascade Sensors of Copper and Glutathione

“…The performance of these sensors was evaluated in comparison to previously reported Cu 2+ and GSH sensors, particularly in terms of K a and LOD values. The results presented in Table demonstrate that the sensors developed in this study offer comparable performance to those reported in the literature, making them promising candidates for copper and glutathione sensing applications. ,,− …”

Fused Nickel(II) Porphyrins—Sensing of Toxic Anions and Selected Metal Ions Through Supramolecular Interactions

“…The adversities associated with metal cations warrant the need for chemical sensors that can easily and selectively detect the cations at low concentrations. A number of mechanistically different sensors are already available to detect different metal ions (Jeong and Yoon, 2012;Kumar et al, 2017). A fluoresceinbased chemosensor has been reported to detect Cu +2 ions in aqueous solutions in nanomolar concentrations (Jun et al, 2006).…”

Multicomponent synthesis of chromophores – The one-pot approach to functional π-systems

“…Another chemosensor but for the detection of Cu(II) ions are furo [2,3-d]pyrimidines-2,4[1H,3H]-diones 85. The chromophores consist of fused furopyrimidine and are generated via multicomponent strategy with a chromophore approach (Supplementary Material S29) (Kumar et al, 2017). The MW assisted three-component reaction of 1,3-dimethylbarbituric acid, benzaldehyde and respective isocyanides corresponding isocyanides proceeds via Knoevenagel condensation, [4 + 1] cycloaddition, and a 1,3-H shift to form two furopyrimidinones in excellent yields.…”