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Colorimetric-fluorescent probe for detecting hypochlorite radical, preparation method and application thereof

A technology for the detection of hypochlorous acid and fluorescent probes, applied in the field of environmental and non-standard explosives detection, can solve the problems of low quantum yield, low molar absorptivity, detection limit, etc., and achieve the effect of simple operation

Active Publication Date: 2019-12-31
XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most fluorescent probes still have disadvantages such as poor detection limit, low quantum yield, low molar absorptivity, delayed oxidation reaction time, and poor anti-interference.

Method used

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  • Colorimetric-fluorescent probe for detecting hypochlorite radical, preparation method and application thereof
  • Colorimetric-fluorescent probe for detecting hypochlorite radical, preparation method and application thereof
  • Colorimetric-fluorescent probe for detecting hypochlorite radical, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] a. Dissolve 5mmol N-phenyldiethanolamine in 50mL organic solvent ether, add 20mmol organic base as triethylamine, add 20mmol acryloyl chloride at 0°C, react at room temperature for 12h, extract, wash with deionized water until neutral and anhydrous After drying over magnesium sulfate, suction filtration and spin-drying, 4.6 mmol of intermediate product 1 (phenylazadiyl) bis(ethane-2,1-diyl) diacrylate was obtained, with a yield of 92%;

[0036] b. Drop 4.6 mmol of phosphorus oxychloride into 23 mmol of N,N-dimethylformamide at 0°C, react for 2 hours, then drop into 4.6 mmol of intermediate product 1 obtained in step a, raise the temperature to 75°C, and react for 12 hours After cooling to room temperature, add the organic solvent diethyl ether, the temperature is 0°C, take 30mmol of anhydrous sodium acetate and dissolve it in 50mL of deionized water to prepare an aqueous solution of sodium acetate, then drop the prepared aqueous solution of sodium acetate into the reacta...

Embodiment 2

[0039] a. Dissolve 5mmol N-phenyldiethanolamine in 50mL organic solvent chloroform, add 10mmol organic base as piperidine, add 10mmol acryloyl chloride at 0°C, react for 12h, extract, wash with deionized water until neutral, anhydrous sulfuric acid After magnesium drying, suction filtration and spin-drying, 4.5 mmol of intermediate product 1 (phenylazadiyl) bis(ethane-2,1-diyl) diacrylate was obtained, with a yield of 90%;

[0040] b. Add 4.5mmol of phosphorus oxychloride dropwise into 22.5mmol of N,N-dimethylformamide at 0°C, react for 2 hours, then drop into 4.5mmol of the intermediate product 1 obtained in step a, raise the temperature to 75°C, and react After 12 hours, cool to room temperature, add organic solvent chloroform, temperature 0°C, take 30mmol anhydrous sodium acetate and dissolve it in 50mL deionized water to prepare an aqueous solution of sodium acetate, then drop the prepared aqueous solution of sodium acetate into the reactant, and react at room temperature f...

Embodiment 3

[0043] a. Dissolve 5mmol N-phenyldiethanolamine in 50mL organic solvent tetrahydrofuran, add 15mmol organic base as pyridine, add 15mmol acryloyl chloride at 0°C, react for 12h, extract, wash with deionized water until neutral, and dry with anhydrous magnesium sulfate , suction filtration and spin-drying, 4.7 mmol of intermediate product 1 (phenylazadiyl) bis(ethane-2,1-diyl) diacrylate was obtained, with a yield of 94%;

[0044] b. Drop 4.7mmol of phosphorus oxychloride into 23.5mmol of N,N-dimethylformamide at 0°C, react for 2 hours, then drop into 4.7mmol of the intermediate product 1 obtained in step a, raise the temperature to 75°C, and react After 12 hours, cool to room temperature, add the organic solvent tetrahydrofuran, the temperature is 0°C, take 30mmol of anhydrous sodium acetate and dissolve it in 50mL of deionized water to prepare an aqueous solution of sodium acetate, then drop the prepared aqueous solution of sodium acetate into the reactant, and react at room t...

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Abstract

The invention provides a colorimetric-fluorescent probe for detecting hypochlorite radical, a preparation method and application thereof. Aldehyde aniline and a 2-(3-cyano-4, 5, 5-trimethylfuran-2(5H)-acyl)acrylonitrile electron-withdrawing group are subjected to Knoevenagel condensation, thus obtaining the colorimetric-fluorescent probe (E)-((4-(2-(4-cyano-5-(dicyanomethylene)-2, 2-dimethyl-2, 5-dihydrofuran-3-yl)vinyl)phenyl)azanediyl)bis(ethane-2, 1-diyl)diacrylate. The response group of the probe to hypochlorite radical is C=C double bond, in a mixed solution of an organic solvent and water, the single probe has a fluorescence emission peak position at 632nm and an ultraviolet absorption peak position at 544nm, and when used for detecting hypochlorite radical, the probe shows obvious fluorescence quenching and fading response, the response speed is high, and real-time detection of hypochlorite radical can be realized; the detection sensitivity is high, and the detection limit is aslow as 0.19microM; and the probe can accurately determine the content of hypochlorite radical in a water sample and non-standard explosive raw material in the environment.

Description

technical field [0001] The invention belongs to the field of detection of environment and non-standard explosives, and provides a colorimetric-fluorescent probe for detecting hypochlorite, a preparation method and application thereof. The colorimetric-fluorescent probe has low detection limit, strong anti-interference and short reaction time, and can realize the purpose of low-cost, real-time colorimetric-fluorescent dual-mode detection of hypochlorite. Background technique [0002] Due to the oxidation of hypochlorite, it is widely used in water purification, pulp bleaching, chloramine production in the pharmaceutical industry and other fields. As a very important reactive oxygen species, hypochlorite plays an irreplaceable role in both living organisms and drinking water. The excessive production or accumulation of hypochlorite in organisms can cause many diseases, such as cardiovascular diseases, inflammatory diseases, cancer and other diseases. In addition, the US FBI ...

Claims

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Application Information

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IPC IPC(8): C07D307/68C09K11/06G01N21/33G01N21/64
CPCC07D307/68C09K11/06G01N21/33G01N21/643C09K2211/1088C09K2211/1007G01N2021/6432
Inventor 蔡珍珍窦新存
Owner XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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