CuAAC-Derived Selective Fluorescent Probe as a Recognition Agent for Pb(II) and Hg(II): DFT and Docking Studies

Citations Over TimeTop 10% of 2022 papers

Abstract

Copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) is a resourceful and stereospecific methodology that has considerably yielded promising 1,2,3-triazole-appended "click" scaffolds with the potential for selective metal ion recognition. Based on "click" methodology, this report presents a chemosensor probe (TCT) based on 4-tert-butylcatechol architecture, via the CuAAC pathway, as a selective and efficient sensor for Pb(II) and Hg(II) ions, categorized as the most toxic and alarming environmental contaminants among the heavy metal ions. The synthesized probe was successfully characterized by spectroscopy [IR and NMR (1H and 13C)] and mass spectrometry. The chemosensing study performed in acetonitrile/water (4:1) solvent media, via UV-vis and fluorescence spectroscopy, established its selective sensitivity for Pb(II) and Hg(II) species among the list of explored metal ions with the limits of detection being 8.6 and 11 μM, respectively. Additionally, the 1H NMR and IR spectra of the synthesized TCT-metal complex also confirmed the metal-ligand binding. Besides, the effect of time and temperature on the binding ability of TCT with Pb(II) and Hg(II) was also studied via UV-vis spectroscopy. Furthermore, density functional theory studies put forward the structural comprehension of the sensor by availing the hybrid density functional (B3LYP)/6311G++(d,p) basis set of theory which was subsequently utilized for investigating its anti-inflammatory potential by performing docking analysis with human leukotriene b4 protein.

Related Papers

• → A Hydrophilic Azacyclooctyne for Cu-Free Click Chemistry(2008)280 cited
• → Azide-Modified Graphitic Surfaces for Covalent Attachment of Alkyne-Terminated Molecules by “Click” Chemistry(2007)207 cited
• → Ion recognition by 1,2,3‐triazole moieties synthesized via “click chemistry”(2022)39 cited
• → Phthalonitriles Functionalized for Click Chemistry. Design, Synthesis and Structural Characterization(2013)14 cited
• → Multivalent Azide‐Functionalized Polypyridyl Ruthenium Complexes and Their DNA Conjugates through Click Chemistry(2017)4 cited