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Sulfite ratiometric fluorescence probe and preparation method thereof

A ratiometric fluorescent probe and sulfite technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as ecological environmental hazards and affecting dissolved oxygen concentration in water, and achieve low cost and simple preparation method , easy-to-achieve effects

Inactive Publication Date: 2015-12-02
SHANDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, industrial wastewater contains too much sulfite, which will seriously affect the concentration of dissolved oxygen in the water, thus causing harm to the ecological environment

Method used

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  • Sulfite ratiometric fluorescence probe and preparation method thereof
  • Sulfite ratiometric fluorescence probe and preparation method thereof
  • Sulfite ratiometric fluorescence probe and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0026] (1) Compound N1, N1 dimethylbenzene-1,4-diamine (5g, 36.7mmol) was dissolved in hydrochloric acid solution (6M, 66mL), then added crotonaldehyde (6.0mL, 73.5mmol), stirred at room temperature After 1 h, acetone (35 mL) was added as solvent and stirred at reflux for 12 h. After the reaction was complete, cool to room temperature, remove the organic phase, neutralize the liquid phase with sodium hydroxide solution to a pH of 7, then add dichloromethane (50mL × 3) to extract 3 times, collect the organic phase, dry over anhydrous sodium sulfate, reduce The solvent was distilled off under pressure to obtain a crude product. Then, the product N,N,2-trimethylquinolin-6-amine was separated and purified by column chromatography (dichloromethane:methanol=1:1).

[0027] (2) Compound N,N,2-trimethylquinolin-6-amine (1mmol) and selenium dioxide (1mmol) were dissolved in dioxane / water (140mL / 14mL) mixed solution, refluxed and stirred for 4h. After the reaction was complete as detec...

Embodiment 2

[0031] (1) Compound N1, N1 dimethylbenzene-1,4-diamine (5g, 36.7mmol) was dissolved in hydrochloric acid solution (6M, 60mL), then added crotonaldehyde (7.5mL, 91.75mmol), stirred at room temperature After 2h, acetone (50mL) was added as solvent and stirred at reflux for 10h. Cool to room temperature after monitoring the reaction by TLC, remove the organic phase, neutralize the liquid phase with sodium hydroxide solution to a pH of 7, then add dichloromethane (50mL×3) to extract 3 times, collect the organic phase, and dry over anhydrous sodium sulfate , The solvent was distilled off under reduced pressure to obtain a crude product. Then, the product N,N,2-trimethylquinolin-6-amine was separated and purified by column chromatography (dichloromethane:methanol=1:1).

[0032] (2) Compound N,N,2-trimethylquinolin-6-amine (1mmol) and selenium dioxide (1.5mmol) were dissolved in dioxane / water (100mL / 12mL) mixed solution and stirred at reflux for 5h. After the reaction was complete ...

Embodiment 3

[0036] (1) Compound N1, N1 dimethylbenzene-1,4-diamine (5g, 36.7mmol) was dissolved in hydrochloric acid solution (6M, 75mL), then added crotonaldehyde (8.99mL, 110mmol), stirred at room temperature for 1.5 After h, acetone (40 mL) was added and the solvent was refluxed and stirred for 10 h. Cool to room temperature after monitoring the reaction by TLC, remove the organic phase, neutralize the liquid phase with sodium hydroxide solution to a pH of 7, then add dichloromethane (50mL×3) to extract 3 times, collect the organic phase, and dry over anhydrous sodium sulfate , The solvent was distilled off under reduced pressure to obtain a crude product. Then, the product N,N,2-trimethylquinolin-6-amine was separated and purified by column chromatography (dichloromethane:methanol=1:1).

[0037] (2) Compound N,N,2-trimethylquinolin-6-amine (1mmol) and selenium dioxide (2mmol) were dissolved in dioxane / water (200mL / 20mL) mixed solution, and stirred at reflux for 4h. After the reactio...

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Abstract

The invention belongs to the technical field of chemical analysis detection, and particularly relates to a sulfite ratiometric fluorescence probe and a preparation method thereof. The molecular structural formula of the sulfite ratiometric fluorescence probe refers to description. The preparation method of the sulfite ratiometric fluorescence probe includes the following steps: reacting N1,N1 dimethyl benzene-1,4-diamine with crotonaldehyde to obtain N,N,2-trimethylquinoline-6-amine; reacting N,N,2-trimethylquinoline-6-amine with selenium dioxide to obtain 6-(dimethylamino) quinoline-2-formaldehyde; reacting 2,3,3-trimethylindoline with iodomethane to obtain 1,2,3,3-tetramethyl-3H-indoliu iodide; reacting 6-(dimethylamino) quinoline-2-formaldehyde and 1,2,3,3-tetramethyl-3H-indoliu iodide with piperidine to obtain the probe. According to the invention, molecular synthesis of the probe is simple, the cost is relatively low, the selectivity to sulfite is good, the preparation method is simple, raw materials are cheap and easy to obtain, and the method is easy to realize.

Description

technical field [0001] The invention belongs to the technical field of chemical analysis and detection, and in particular relates to a sulfite ratio fluorescent probe and a preparation method thereof. Background technique [0002] Sulphite is an important food additive. A small amount of sulphite intake by humans will not cause harm to the body. However, excessive intake of sulphite may cause gastrointestinal disorders, severe abdominal pain, and renal dysfunction. Especially for people who are allergic to sulfites, even a small amount of sulfites can easily cause asthma, skin allergies, and gastrointestinal discomfort. In addition, industrial wastewater contains too much sulfite, which will seriously affect the concentration of dissolved oxygen in the water, thus causing harm to the ecological environment. Therefore, it is very important to invent a convenient, quick and highly sensitive method for detecting sulfite content for food safety and environmental detection. Co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D401/06G01N21/64
Inventor 陈志伟孙娟连志敏王苏
Owner SHANDONG UNIV OF TECH
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