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A near-infrared colorimetric and fluorescent dual-channel probe for cyanide detection based on dicyanomethylene-4H-pyran
- Source :
- Inorganic Chemistry Communications. 122:108245
- Publication Year :
- 2020
- Publisher :
- Elsevier BV, 2020.
-
Abstract
- A novel dicyanomethylene-4H-pyran-based sensor bearing 2-thiophenecarbonyl as a masking group was established for the detection of cyanide anions. Upon the addition of cyanide, sensor 1 manifested a near-infrared emission band at 717 nm, with an extremely large red-shift (~180 nm) in the absorption spectrum. It also showed an obvious color change from yellow to green. Sensor 1 was used to sensitively measure CN− with low detection limit of 1.44 μM. The stoichiometric ratio between probe and CN− were determined as 1:1, with the association constant of 7.87 × 102 M−1. The reaction mechanism was investigated by ESI-MS, 1H NMR, HPLC, and density functional theory methods. Results indicate that the nucleophilicity of the cyanide catalyzes the elimination of 2-thiophenecarbonyl, which strengthens the intramolecular charge transfer effect of the dicyanomethylene-4H-pyran fluorophore. Furthermore, sensor 1 was found to be efficient in detecting cyanide in the intracellular region of MCF-7 cells.
- Subjects :
- Detection limit
Fluorophore
Absorption spectroscopy
Chemistry
Cyanide
02 engineering and technology
010402 general chemistry
021001 nanoscience & nanotechnology
Photochemistry
01 natural sciences
Fluorescence
0104 chemical sciences
Inorganic Chemistry
chemistry.chemical_compound
Nucleophile
Pyran
Materials Chemistry
Proton NMR
Physical and Theoretical Chemistry
0210 nano-technology
Subjects
Details
- ISSN :
- 13877003
- Volume :
- 122
- Database :
- OpenAIRE
- Journal :
- Inorganic Chemistry Communications
- Accession number :
- edsair.doi...........80055fa2d8c8e3bf25203e48eceb01f0