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2-Azahetaryl-2-(oxoindolin-2-ylidene)acetonitriles as Colorimetric Probes for Zn: Synthesis and Optical Properties

Authors :
Vladyslav V. Shcherban
Olena O. Kuleshova
Tetiana Ye. Keda
Olga V. Khilya
Emmanuel Gras
Yulian M. Volovenko
Taras Shevchenko National University of Kyiv
Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA)
Institut de Chimie de Toulouse (ICT)
Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3)
Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP)
Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3)
Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)
Source :
ACS Omega, ACS Omega, In press, ⟨10.1021/acsomega.2c04747⟩
Publication Year :
2022
Publisher :
American Chemical Society (ACS), 2022.

Abstract

International audience; A new one-pot approach for the synthesis of the Zn2+-sensitive probes 2-azahetaryl-2-(oxoindolin-2-ylidene)acetonitriles 3a–c and 4 is described. The method includes the in situ formation of imidoylchloride and its further condensation with azahetarylacetonitrile 1. The structure of the obtained compounds is studied using 1H nuclear magnetic resonance (NMR), 13C NMR, infrared (IR), high-resolution mass spectrometry (HRMS), and UV–Vis spectroscopy techniques. Two model ligands both exhibiting the highest extinction coefficient and the best solubility in a Tris buffer pH 7.2/dimethyl sulfoxide (DMSO) solution, namely 5-methyl-benzothiazole derivative 3b and benzoxazole derivative 4, are thoroughly studied as colorimetric probes for Zn2+. The probe 3b has the highest sensitivity to Zn2+, showing a limit of ion detection (LOD) calculated by the 3S criterion of 0.43 μM and selectivity upon masking Cu2+ ions with Na2S2O3. The composition of the complexes in the solution was determined by the limited logarithm method. The stability constant (lg K) values of 3b-Zn of 10.27 ± 0.02 and 4-Zn of 12.5 ± 0.2 indicate the formation of complexes of average stability.

Details

ISSN :
24701343
Volume :
7
Database :
OpenAIRE
Journal :
ACS Omega
Accession number :
edsair.doi.dedup.....26814e5754ecaed67eda9c28ca05af91