Organic small molecular fluorescent probe for detecting methanol and preparation method of organic small molecular fluorescent probe

A fluorescent probe and small molecule technology, applied in the field of chemical substance synthesis, can solve the problems of unsuitable for rapid determination, lengthy steps, complicated operation, etc., and achieve the effects of mild conditions, convenient operation and strong response

Inactive Publication Date: 2016-09-28
北京珐默兹医药科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, although there are many methods for detecting methanol content, such as; gas chromatography and atomic absorption spectrometry, etc., although these methods are accurate and sensitive, the steps are lengthy, the operation is cumbersome, and the time is long, so they are not suitable for rapid determination.

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  • Organic small molecular fluorescent probe for detecting methanol and preparation method of organic small molecular fluorescent probe
  • Organic small molecular fluorescent probe for detecting methanol and preparation method of organic small molecular fluorescent probe
  • Organic small molecular fluorescent probe for detecting methanol and preparation method of organic small molecular fluorescent probe

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preparation example Construction

[0016] A kind of preparation method of the organic small molecule fluorescent probe that detects methanol of the present invention, comprises the following steps:

[0017] Step 1: Preparation of 1-(p-toluenesulfonyl) imidazole: add dichloromethane and sodium bicarbonate aqueous solution in reaction flask, stir to form solution A, wherein, the volume ratio of dichloromethane and sodium bicarbonate aqueous solution is 3: 5; Add imidazole and tosyl chloride to solution A, the mass ratio of imidazole to p-toluenesulfonyl chloride is 1:3, and the mass volume ratio of tosyl chloride to dichloromethane is 1:4g / mL; After imidazole and p-toluenesulfonyl chloride were dissolved, triethylamine was added to the above solution, and the triethylamine accounted for 0.7% by volume of solution A, and stirred at room temperature for 12 hours; the aqueous phase after liquid separation was extracted with dichloromethane, organic The phase is dried with anhydrous magnesium sulfate, the filtrate is...

Embodiment 1

[0019] Embodiment 1: The preparation of organic small molecule fluorescent probes for detecting methanol is as follows:

[0020] Step 1. Preparation of 1-(p-toluenesulfonyl)imidazole: Add 150mL dichloromethane and 250mL aqueous sodium bicarbonate solution into the reaction flask, start stirring, then add 12.75g imidazole and 38.25g p-toluenesulfonyl chloride, and wait for the solid to dissolve Finally, 3 mL of triethylamine was added to the above solution, and stirred at room temperature for 12 hours; the aqueous phase after liquid separation was extracted with dichloromethane, the organic phase was dried with anhydrous magnesium sulfate, and the filtrate was obtained by suction filtration, concentrated by rotary evaporation to 50 mL, and added 13 mL of a low-polarity organic solvent was left to stand overnight to obtain a crude product, which was filtered and washed twice with a low-polarity organic solvent, and the obtained crystals were vacuum-dried at 30°C for 6 hours to ob...

Embodiment 2

[0023] Embodiment two: if figure 2 As shown, the fluorescence emission spectra of the fluorescent probe prepared in the present invention in different solvents are as follows, wherein the fluorescence detection condition is a slit width of 2.5 / 2.5. The detection method of methanol is a fluorescence detection method, and the maximum emission wavelength is different under the same excitation wavelength of the substance in different solvents, and the fluorescence intensity is also different. It can be used for the determination of methanol content in different solvents, and can quickly detect the content of methanol.

[0024] (1) At room temperature, weigh 0.02g of the fluorescent probe of the present invention prepared in advance, soak it in 100mL of n-hexane for two minutes, filter it quickly, prepare a sample for testing, the excitation wavelength is 320nm, and the emission wavelength is 375nm. The fluorescence intensity was 30, and the emission wavelength curve of the probe...

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Abstract

The invention discloses a preparation method of an organic small molecular fluorescent probe for detecting methanol. The preparation method comprises the following steps: firstly, preparing 1-(p-toluenesulfonyl) imidazole; secondly, preparing the organic small molecular fluorescent probe: adding a proper amount of 4-bromotriphenylamine and the 1-(p-toluenesulfonyl) imidazole into a tetrahydrofuran solution, and then adding a catalyst consisting of copper sulfate pentahydrate and sodium ascorbate into the solution; protecting by nitrogen and stirring for 12 hours, extracting with dichloromethane, drying by using anhydrous magnesium sulfate, and performing rotary evaporation to obtain a crude product; performing column chromatographic separation on the crude product by using ethyl acetate and petroleum ether, wherein the volume ratio of the ethyl acetate to the petroleum ether is 1 to (10 to 20), and separating to obtain a solid, namely the organic small molecular fluorescent probe for detecting the methanol. The fluorescent probe disclosed by the invention has a high fluorescent selective response to the methanol; the fluorescence intensity is remarkably enhanced along with the prolonging of time; the organic small molecular fluorescent probe has the advantages of easiness in preparation, good chemical stability, high sensitivity and the like.

Description

technical field [0001] The invention belongs to the fields of chemical substance synthesis, fluorescence sensing and fluorescence analysis, and in particular relates to an organic small molecule fluorescent probe capable of identifying the methanol content in a solvent, especially the methanol content test in ethanol. The invention belongs to the fields of chemical substance synthesis, fluorescence sensing and fluorescence analysis. Background technique [0002] Methanol is a colorless, volatile liquid with an alcoholic odor. It is often used by criminals in the preparation of alcohol to make huge profits and cause serious harm. Studies have shown that the lowest dose of human oral poisoning is about 100mg / kg body weight, and oral intake of 0.3-1g / kg can be fatal. Because methanol will be oxidized into formaldehyde and formic acid (formic acid), which are more toxic than methanol, in human metabolism, drinking wine containing methanol can cause blindness, liver disease, an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/56C07D249/04C07D249/08G01N21/64
CPCC07D233/56C07D249/04C07D249/08G01N21/643
Inventor 王勇武志花
Owner 北京珐默兹医药科技有限公司
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