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A Fluorescent Probe for Rapid Recognition of Thiophenol

A fluorescent probe and thiophenol technology, which is applied in the field of chemical analysis, can solve the problems of poor water solubility, weak anti-interference ability, and insufficient response speed of fluorescent probes, and achieves strong anti-interference ability, rapid response, and fast response speed. quick effect

Active Publication Date: 2020-01-24
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Moreover, although the current thiophenol fluorescent probes have realized the detection of thiophenol in living cells, the response speed to thiophenol in the detection process is not fast enough, and at the same time, most of the fluorescent probes are relatively water-soluble. Poor and anti-interference ability is not strong, which leads to the limitation of its scope of use

Method used

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  • A Fluorescent Probe for Rapid Recognition of Thiophenol
  • A Fluorescent Probe for Rapid Recognition of Thiophenol
  • A Fluorescent Probe for Rapid Recognition of Thiophenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] A method for preparing a fluorescent probe for rapid detection of thiophenol, specifically comprising the following steps:

[0038] Synthesis of Intermediate A: Dissolve 1 g (6.84 mmol) of 2,7-naphthyridin-1(2H)-one and 9.81 g (34.21 mmol) of phosphorus oxybromide in 10 mL of acetonitrile and heat to 80 ℃ for 1 h. Add ice water to the reaction system to quench the phosphorus oxybromide, then adjust the pH to neutral. The solution was extracted 3 times with dichloromethane, then with Na 2 SO 4 The dichloromethane extract was dried and distilled under reduced pressure to obtain a red crude product, which was further purified by silica gel column chromatography to obtain a white solid, namely intermediate A (980 mg, yield 69%). 1H NMR (400 MHz, CDC13): δ 9.76 (s, 1H), 8.82 (d, J = 4 Hz, 1H),8.48 (d, J = 4 Hz, 1H), 7.68 (d, J = 8 Hz, 1H), 7.61 (d, J = 8 Hz, 1H).

[0039] Synthesis of Intermediate B: Under argon, 400 mg (1.91 mmol) of Intermediate A and 134 mg (0.19 mmo...

Embodiment 2

[0046] The effect of the fluorescent probe obtained in Example 1 reacting with thiophenol was determined.

[0047] A 100 μM fluorescent probe solution in Example 1 was prepared using 10 mM PBS (pH=7.4) buffer solution, and a 10 mM thiophenol stock solution was prepared with acetonitrile. Take 100 μL of the above-mentioned fluorescent probe solution and 900 μL PBS (pH=7.4) buffer solution in a cuvette, and detect its fluorescence spectrum under 355 nm excitation, as shown in Figure 4 The solid line part; take 100 μL of the above compound f solution, 895 μL of PBS (pH=7.4) buffer solution and 5 μL of thiophenol stock solution in a cuvette, and detect its fluorescence spectrum under 355 nm excitation, as shown in Figure 4 imaginary part.

[0048] from Figure 4 Comparing the dotted line and the solid line, it can be seen that the background of the fluorescent probe is low and the response to thiophenol is strong, which is a fluorescence-enhanced thiophenol probe.

Embodiment 3

[0050] The analysis of the reaction of the fluorescent probe obtained in Example 1 with different concentrations of thiophenol was determined.

[0051] Add 100 μL of fluorescent probe solution and PBS (pH=7.4) buffer solution to the cuvette, and then add working concentrations of 0, 2, 4, 6, 8, 10, 20, 40, 60, 80, 90 , 100 μM thiophenol was prepared into a 1 mL reaction system, and the fluorescence spectra of different concentrations of thiophenol reacted with the fluorescent probe for 30 seconds were measured, as shown in Figure 5 shown.

[0052] from Figure 5 It can be seen that within a certain concentration range, the fluorescence intensity of the reaction system at 580 nm increases with the concentration of thiophenol, indicating that the probe can detect thiophenol at different concentrations.

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Abstract

The invention discloses a fluorescent probe for rapidly recognizing thiophenol. The fluorescent probe reacts with thiophenol to generate a reaction product with strong fluorescence. This fluorescent probe can interact with thiophenol through the 2,4-dinitrophenyl ether group recognition group with strong electron-withdrawing ability. Phenol reacts quickly, and produces a reaction product with strong fluorescence at the same time, with high sensitivity and fast response speed; because the fluorescent probe has strong anti-interference ability and can specifically recognize thiophenol, it is suitable for various Thiophenol detection of samples.

Description

technical field [0001] The invention relates to the technical field of chemical analysis, in particular to a fluorescent probe for rapidly identifying thiophenol. Background technique [0002] Thiophenol (PhSH) is a highly toxic pollutant that widely exists in the preparation of pharmaceuticals, pesticides and chemical intermediates. Thiophenol can cause a series of serious harm to other organisms such as humans, mice, and fish through inhalation, ingestion, and percutaneous absorption. Thiophenol has a strong irritating effect on eyes and skin; it can cause breathing difficulties, coma and even death; high concentration of thiophenol can cause the death of fish and mice. Therefore, establishing a specific detection method for thiophenol in the environment and in organisms has important practical application value. [0003] At present, the detection methods of thiophenol include high performance liquid chromatography, gas chromatography, electrochemical method, ultraviolet...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C09K11/06G01N21/64
CPCC07D471/04C09K11/06C09K2211/1029G01N21/643
Inventor 孙琦佘能芳任瑞
Owner WUHAN INSTITUTE OF TECHNOLOGY
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