Fluorescent probe and preparation method and application thereof

A technology of fluorescent probes and probes, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of complex synthesis, poor water solubility, insufficient selectivity and sensitivity, etc., and achieve high luminous intensity and stable performance , cheap effect

Active Publication Date: 2020-05-29
HUNAN ZHONGDA CONSTR ENG TESTING TECH
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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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  • Fluorescent probe and preparation method and application thereof
  • Fluorescent probe and preparation method and application thereof
  • Fluorescent probe and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Dissolve compound A (0.76g, 2.12mmol) and 4-pyridineacetonitrile (0.25g, 2.12mmol) in absolute ethanol (10mL), then add piperidine (0.1mL) to the reaction solution, and reflux at 80°C React for 5 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 0.838 g of a yellow solid ( The yield was 86%). After the product is analyzed by proton nuclear magnetic resonance spectrum, its structural formula is as shown in formula (1):

[0042]

[0043] Wherein the structural formula of compound A is as shown in formula (2):

[0044]

[0045] The H NMR spectrum is as figure 1 As shown, the description of the spectrum is as follows:

[0046] 1 H NMR (400Hz, CDCl 3 ): 1 H NMR (400MHz, CDCl 3): δ8.96(s,1H), 8.71(s,2H), 8.54(s,1H), 8.11(s,1H), 7.51(s,2H), 7...

Embodiment 2

[0048] Compound A (0.76g, 2.12mmol) and 4-pyridineacetonitrile (0.25g, 2.12mmol) were dissolved in anhydrous acetonitrile (10mL), then triethylamine (0.1mL) was added to the reaction solution, and at 50°C Reflux for 5 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 0.563 g of a yellow solid ( Yield 57%).

Embodiment 3

[0050] Dissolve compound A (0.76g, 2.12mmol) and 4-pyridineacetonitrile (0.25g, 2.12mmol) in absolute ethanol (10mL), then add sodium acetate (0.1mL) to the reaction solution, and reflux at 80°C React for 12 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 0.746 g of a yellow solid ( Yield 76%).

[0051] Fluorescent detection of thiophenol with fluorescent probes:

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Abstract

The invention discloses a fluorescent probe and a preparation method thereof, the fluorescent probe has a chemical structural formula shown in a formula (1), and the preparation method of the fluorescent probe specifically comprises the following steps: (1) preparing raw materials; (2) dissolving 4-(diethylamino)-2-(2, 4-dinitrophenoxy)-benzaldehyde, pyridylacetonitrile and a catalyst in a solvent, and carrying out a heating reaction for 1-24 h to obtain a mixed solution; and (3) removing the solvent from the mixed solution, and performing separating through a chromatographic column to obtainthe fluorescent probe. The fluorescent probe molecule provided by the invention has good stability and optical properties, high selectivity and high sensitivity, strong thiophenol recognition capability, the high response speed, the wide response range and low detection limit; and according to the preparation method of the fluorescent probe, the used raw materials are easy to obtain, the synthesisyield is high, the reaction conditions are mild, the equipment is simple, and the steps are simple and convenient.

Description

technical field [0001] The invention belongs to the technical field of chemical analysis and detection, and in particular relates to a fluorescent probe and its preparation method and application. 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 sensitivity and high selectivity. [0003] Fluorescence detection ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/57C09K11/06G01N21/64
CPCC07D213/57C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029G01N21/64G01N21/6428G01N21/6456G01N2021/6417
Inventor 李学强孙圣梁波夏旭伟张雅南
Owner HUNAN ZHONGDA CONSTR ENG TESTING TECH
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