Spectroscopic investigation of bis-appended 1,2,3-triazole probe for the detection of Cu(II) ion

Abstract

A novel bis-1,4-disubstituted-1,2,3-triazole chemosensor, accessed with "Click Chemistry", was probed for its recognition of metal ions. The interaction of the sensor with various cation analytes was investigated by 1 H-NMR, UV-Vis absorption and fluorescence spectroscopy. The bis-triazole is selective for Cu(II) with a detection limit in the micromolarconcentration range and a clear to yellow colorimetric response that is exclusive to that ion is observed. The stoichiometry of probe to Cu(II), 2 : 1, was determined with Job's plots based on titration studies using UV-absorption and 1 H-NMR spectroscopy. Computational and spectroscopic investigations revealed that the sensor binds to Cu(II) via its triazole units. Keywords: , there are less reports for bis-triazole sensors that provide a colorimetric signal.(43) Additionally, in many instances the bistriazole sensors fail to respond exclusively to Cu(II).(31, 34, 37, 38) Herein, we report the synthesis of a novel bis-1,2,3triazole sensor appended with phenolic groups, (2,2-bis((1-(2hydroxyphenyl)-1H-1,2,3-triazol-4-yl)methyl)-5,5dimethylcyclohexane-1,3-dione) (BPT) (Scheme 1). BPT exhibits a selective colorimetric response to copper(II), clear to yellow. To verify the selectivity, BPT was screened against an series of metal ions

Nuclear Magnetic Resonance Spectroscopy Investigations of Naphthalene-Based 1,2,3-Triazole Systems for Anion Sensing

“…It also suggests that the fluoride anion is in close vicinity to the triazole proton and the -OH proton, shown in Scheme 2. The single X-ray crystal structure for NpTP and our previous studies on cation sensor (BPT) [56] also support this hypothesis. The crystal structure substantiated that there is no intramolecular hydrogen bonding between the phenolic oxygen (-OH) and the triazole proton (see Section 2.4).…”

Exploring the Effects of Various Polymeric Backbones on the Performance of a Hydroxyaromatic 1,2,3-Triazole Anion Sensor

“…Eventually, the resonances of H-8, H-6, and H-4 broadened out into the baseline of the spectra. Consistent with the behavior of PTP and similar molecules [14,21,24,25], these changes in the H-8 and phenol group's chemical shifts indicated coordination between P01′s −OH unit and F − (Scheme 2 and Figure 2). Thus, the non-fluorometric response of P01 was solely due to the quenching effect of the nitro group [29][30][31].…”

“…1,2,3-Triazoles have shown excellent promise as sensors for cation and anion recognition [13][14][15]. These structures are N-donors in cation-sensing [14,16] and Csp 2 -H hydrogen bond donors in anion-sensing [17][18][19]. Triazoles are easily synthesized from azide and alkyne precursors via copper-catalyzed azide-alkyne cycloaddition (CuAAC) (Scheme 1) [20].…”

A new benzimidazole‐based selective and sensitive ‘on–off’ fluorescence chemosensor for Cu2+ ions and application in cellular bioimaging

“…Among them, the copper(II) ion (Cu 2+ ) is an essential trace element in biological and fundamental physiological processes, such as a cofactor in a great many enzymes . On the contrary, overloading Cu 2+ ions in the human body can induce neurodegenerative diseases such as Menkes, Alzheimer and Parkinson . Therefore, the development of new methods to recognize and detect Cu 2+ ions at lower concentration and with higher sensitivity in the environment and biological systems has become more important.…”