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Novel carbazole fluorescent thiol marking reagent as well as synthesis method and application thereof

A technology for labeling reagents and synthesis methods, which is applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problem of high instrument cost, and achieve the effects of high labeling yield, short labeling time, and mild labeling conditions.

Inactive Publication Date: 2018-09-04
QUFU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the signal interference of mass spectrometry is relatively strong, and the cost of the instrument is high, requiring specialized technical operators, which limits the application of mass spectrometry in the detection of organophosphorus pesticides to a certain extent.

Method used

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  • Novel carbazole fluorescent thiol marking reagent as well as synthesis method and application thereof
  • Novel carbazole fluorescent thiol marking reagent as well as synthesis method and application thereof
  • Novel carbazole fluorescent thiol marking reagent as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of (4-(9H-carbazol-9-yl)benzylidene)malononitrile

[0030] (1) Add 10g carbazole, 13.2g 4-bromobenzaldehyde, 5g potassium carbonate, 2.5g cuprous iodide and 2g18-[crown]-6 ether in a 250mL three-necked flask, add 150mL dimethyl sulfoxide as a solvent, Oil bath 130 ℃ reacted 24h; After the reaction was finished, the reaction solution was cooled to room temperature, suction filtered, then the suction filtrate was mixed with 20wt% NaCl aqueous solution to precipitate a solid, the solid was recovered and dried, and recrystallized 3 times with acetonitrile to obtain the intermediate ( 4-(9H-carbazol-9-yl)benzaldehyde, the yield is 85%;

[0031] (2) Add 7.5g (4-(9H-carbazol-9-yl) benzaldehyde to a 100ml three-necked flask equipped with electromagnetic stirring, completely dissolve with 20mL of anhydrous acetonitrile, 2mL of anhydrous pyridine as a catalyst, and then add 2.8 g malononitrile, heating and reflux reaction 4h, after the reaction finished, the reaction...

Embodiment 2

[0036] The thiol degradation products of organophosphorus thiol ester insecticides are marked by fluorescent thiol labeling reagents, so as to realize the quantitative analysis of organophosphorus thiol ester insecticides, except for the complete detection of organophosphorus thiol ester insecticides. In addition to hydrolysis and complete labeling of degraded thiol products, accurate acquisition of the fluorescence maximum excitation and maximum emission wavelengths of labeling reagents and degraded thiol product markers is the key to improving detection sensitivity and reducing detection limits.

[0037] The invention utilizes the nucleophilic substitution reaction between phenylbutane-1,2,3-triketone-2-oxime and organophosphorus thiol ester insecticides to release and degrade the hydrolyzed organophosphorus thiol ester insecticides Mercaptan products, by optimizing the amount of phenylbutane-1,2,3-trione-2-oxime and organophosphorus thiol ester insecticides, the complete pro...

Embodiment 3

[0040] (1) Utilize (4-(9H-carbazol-9-yl)benzylidene)malononitrile to fluorescently label the degraded thiol products of organophosphorus thiol ester pesticides to realize the organophosphorus thiol esters in agricultural products For the quantitative analysis of pesticides, prepare 2.0nM phenylbutane-1,2,3-trione-2-oxime solution and use it to catalyze the hydrolysis of organophosphorus thiol ester pesticides to produce degraded thiol products. Prepare 5 parts of solutions of organophosphorus thiol ester insecticide standards, the concentrations are respectively 1 μM, 10 μM, 100 μM, 1 mM, 10 mM; The acetonitrile solution of methyl) malononitrile, the 4-dimethylaminopyridine solution of preparation 3.0nM, provides suitable alkaline environment for the labeling reaction of labeling reagent and the thiol degradation product of organophosphorus thiol ester insecticide;

[0041] (2) Add 100 μL of the standard solution of organophosphorus thiol ester insecticides and 200 μL of pheny...

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Abstract

The invention provides a novel carbazole fluorescent thiol marking reagent as well as a synthesis method and application thereof. The florescent marking reagent adopts carbazole as a fluorescent basering and activated C=C double bonds as reaction activity groups, is simple and convenient in synthesis step, easy to operate and can be synthesized in a large scale through two steps of reactions as follows: (1) enabling carbazole to react with 4-bromobenzaldehyde so as to obtain an intermediate (4-(9H-carbazole-9-yl) benzaldehyde; (2) enabling the intermediate (4-(9H-carbazole-9-yl) benzaldehydeto react with malononitrile so as to obtain a target product (4-(9H-carbazole-9-yl) benzaldehyde malononitrile, and performing recrystallization for three times with acetonitrile, thereby obtaining ayellow needle-shaped crystal. The chemical purity of the fluorescent marking reagent provided by the invention is up to 99%, and the fluorescent marking reagent is stable in chemical property. The novel carbazole fluorescent thiol marking reagent provided by the invention is capable of rapidly and accurately marking degradation thiol products of organic thiol ester insecticides under a gentle condition, and quantitative analysis on contents of organic thiol ester insecticides in reagent samples can be achieved.

Description

technical field [0001] The invention belongs to the technical field of organic small molecule fluorescent labeling, and in particular relates to a synthesis method of a novel carbazole fluorescent labeling reagent and its application in the detection of organophosphorus thiol ester insecticides. Background technique [0002] Organophosphorus pesticides are widely used in agricultural production. They are the most effective way to prevent pests and diseases, and they are also an effective way to increase food production to meet the needs of the growing population. However, there are also potential residues of organophosphorus pesticides due to their overuse in agriculture. The presence of organophosphate pesticide residues is an important issue in food safety. Humans may cause damage to the immune and endocrine systems by ingesting low concentrations of organophosphate pesticide residues. Acute exposure can cause weakness or muscle paralysis, while chronic exposure can affe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C09K11/06G01N21/64
CPCC07D209/86C09K11/06C09K2211/1007C09K2211/1029G01N21/643
Inventor 尤进茂于延新王博谭江坤金倩倩王雨晴李建明纪仲胤
Owner QUFU NORMAL UNIV
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