1H-indole-based chemosensors for the sequential recognition of Hg2+ and CN− ions
| Autor: | I. O. Tupaeva, Eugeny A. Gusakov, Irina V. Dubonosova, Andrey G. Starikov, Alexander D. Dubonosov, Olga Yu. Karlutova, Yury A. Sayapin, Valerii V. Tkachev, Sergey M. Aldoshin |
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| Rok vydání: | 2021 |
| Předmět: |
Indole test
Molecular switch 010405 organic chemistry Organic Chemistry 010402 general chemistry Photochemistry 01 natural sciences Biochemistry Fluorescence 0104 chemical sciences Ion chemistry.chemical_compound chemistry Absorption band Drug Discovery Bathochromic shift Absorption (chemistry) Acetonitrile |
| Zdroj: | Tetrahedron. 84:132030 |
| ISSN: | 0040-4020 |
| Popis: | Сhemosensors based on 1H-indole, 1H-benzo[e]indole, and 1H-benzo[g]indole were synthesized. According to 1H, 13C NMR, X-ray diffraction study and DFT calculations, they exist predominantly in keto form, which absorbs at 371–404 nm and exhibit a low-intensity fluorescence at 454–527 nm. Recognition of Hg2+ cations in acetonitrile results in a bathochromic shift of the long-wave absorption band by ∼20 nm, accompanied by a “naked-eye” effect that causes the colorless solution to turn bright yellow. At the same time, the emission of sensors is completely quenched. The in situ mercury(II) complexes sequentially and selectively detect CN− anions with full restoration of the initial absorption and fluorescence spectra. The fluorescence “on–off–on” cycles generated by the consistent addition of Hg2+ and CN− ions provide the obtained compounds with the properties of ionochromic molecular switch. The values of the limit of detection are 1.8 and 0.83 μМ for Hg2+ and CN− ions, respectively. |
| Databáze: | OpenAIRE |
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