Reactive fluorescent probe for detecting thiophenol and synthesis method and application thereof

A fluorescent molecular probe, thiophenol technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of complex synthesis, insufficient selectivity and sensitivity, poor water solubility, etc., and achieve stable optical performance. , high sensitivity, high synthesis yield effect

Active Publication Date: 2020-05-12
SHANGQIU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the fluorescent probe molecules currently used to detect thiophenols still have problems such as complex synthesis, insufficient selectivity and sensitivity, and poor water solubility (Zhang W.J. Dyes and Pigments 2016, 133, 248; Pagidi S. Langmuir 2018, 34, 8170; Genga Y.Sensors&Actuators:B.Chemical 2018,273,1670.), therefore, it is urgent to develop a thiophenol detection probe with excellent performance to overcome the above problems

Method used

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  • Reactive fluorescent probe for detecting thiophenol and synthesis method and application thereof
  • Reactive fluorescent probe for detecting thiophenol and synthesis method and application thereof
  • Reactive fluorescent probe for detecting thiophenol and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: Synthesis of Fluorescent Molecular Probes

[0034] Dissolve compound 2 (0.2g, 0.522mmol) and 4-pyridineacetonitrile (0.05g, 0.522mmol) in absolute ethanol (10mL), then add piperidine (0.1mL) to the reaction solution, and reflux at 80°C React for 6 hours. After the reaction was finished, the filtrate was removed by suction filtration, and the filter cake was retained, purified by column chromatography, and the eluent was dichloromethane / ethyl acetate (1:1, volume ratio), and spin-dried under reduced pressure to obtain 0.221 g of a yellow solid ( Yield: 88%). The product structural formula is as follows:

[0035]

[0036] 1 H NMR (400Hz, CDCl 3 ): δ8.81(d, J=2.7Hz, 1H), 8.56(d, J=4.8Hz, 2H), 8.29(dd, J=9.3, 2.7Hz, 1H), 8.14(s, 1H), 7.78 (s,1H),7.40(d,J=6.2Hz,2H),6.84(d,J=9.3Hz,1H),3.36(t,J=5.4Hz,2H),3.33–3.27(m,2H) ,2.85(d,J=6.3Hz,2H),2.74(s,1H),2.22(s,1H),2.03(dt,J=11.9,6.0Hz,2H),1.92(dd,J=11.7,6.0 Hz,2H).( figure 1 ). MS[ESI]:m / z, calcd for[M+H] ...

Embodiment 2

[0037] Example 2: Fluorescent detection of probes to thiophenol

[0038] The molecular probe prepared above was dissolved in a phosphoric acid mixed buffer solution (10 mM, pH 7.4) to prepare 10 μmol L -1 probe solution. Add 2 mL of prepared 10 μmol L to a 3 mL cuvette -1 Probe solution of the present invention, then add different concentrations of thiophenol and mix evenly, test its fluorescence spectrum, the results are as follows figure 2 shown. The fluorescence emission intensity of the solution at 545nm is plotted against the concentration of thiophenol, and the concentration of thiophenol is 0–12 μmol L -1 In the range, there is a good linear relationship between the two ( image 3 ), the quantitative detection of thiophenol in this concentration range can be realized. And this probe is not affected by some other common substances, such as sodium nitrate, copper chloride, cysteine, glutathione, homocysteine, sodium carbonate, sodium sulfide, sodium acetate, sodium ...

Embodiment 3

[0039] Embodiment 3: the test of probe of the present invention to thiophenol in the cell

[0040]After cultured human gastric cancer cells (MGC-803) were cultured in 10 μM PBS solution of the probe of the present invention at 37° C. for 1 h, the cell images obtained had no fluorescence. However, MGC-803 cells were cultured at 37°C for 1 h in the culture solution containing the probe of the present invention, then added thiophenol, and cultured with the solution containing thiophenol for 1 h, after being washed with PBS buffer, the fluorescence of the cells could be obtained. imaging, see attached Figure 5 . This shows that the probe of the present invention has good cell membrane permeability and can be used for cell imaging analysis in the field of biomedicine.

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Abstract

The invention discloses a near-infrared fluorescent probe for detecting thiophenol and a synthesis method and application of the near-infrared fluorescent probe, and belongs to the technical field ofchemical analysis and detection. The probe disclosed by the invention is obtained by a reaction between 8-(2, 4-dinitrophenoxy) julolidin-9-formaldehyde and 4-pyridine acetonitrile; the probe has thefollowing structure as shown in the specification; the response group of the probe to thiophenol is 2, 4-dinitrophenoxy, and the probe and thiophenol react to further generate an intramolecular cyclization reaction to generate coumarin fluorescent molecules with strong fluorescence emission, thereby implementing fluorescence detection on thiophenol. The probe molecule has high selectivity and sensitivity to thiophenol, the detection range is 0-12 [mu] mol.L <-1>, and the detection limit is 33 nmol.L <-1>. The probe can be used for detecting thiophenol in water, soil and cells.

Description

technical field [0001] The invention belongs to the technical field of chemical analysis and detection, and in particular relates to a reactive fluorescent probe for detecting thiophenol, a synthesis method thereof and an application in detecting thiophenol. Background technique [0002] Thiophenol (C 6 h 5 SH, PhSH) is a highly reactive aryl sulfide, which is widely used in the synthesis industry, such as the synthesis of sulfa drugs, pesticides and polymers. But on the other hand, thiophenol is highly toxic, and inhalation and skin intake can lead to various diseases, such as dyspnea, muscle weakness, central nervous system damage and even death. The U.S. Occupational Safety and Health Administration limits the maximum concentration of thiophenol in the working environment to 0.1ppm. With the large amount of industrial use of thiophenols, emissions and toxic effects, it is very necessary to develop a method for the detection and protection of thiophenols with high sensi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06C09K11/06G01N21/64
CPCC07D471/06C09K11/06G01N21/6428C09K2211/1029C09K2211/1007G01N2021/6439
Inventor 郝远强张银堂董辉韩华博韦秀华朱旭瞿鹏徐茂田
Owner SHANGQIU NORMAL UNIVERSITY
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