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A kind of hydrogen peroxide fluorescent probe and its preparation method and application

A hydrogen peroxide and fluorescent probe technology, applied in the field of chemical analysis and detection, can solve the problems of slow response, small Stokes shift value, complex synthesis, etc., and achieve fast response speed, large Stokes shift value, highly responsive effect

Active Publication Date: 2021-03-23
HUNAN ZHONGDA CONSTR ENG TESTING TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most of the currently reported fluorescent probe molecules for the detection of hydrogen peroxide have complex synthesis, slow response, need to use organic solvents, and small Stokes shift values ​​(Ren M, Analytical Chemistry, 2017, 89, 552; Chan J, Nature Chemistry, 2012, 4, 973.) and other issues

Method used

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  • A kind of hydrogen peroxide fluorescent probe and its preparation method and application
  • A kind of hydrogen peroxide fluorescent probe and its preparation method and application
  • A kind of hydrogen peroxide fluorescent probe and its preparation method and application

Examples

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Effect test

Embodiment 1

[0042] Compound A (0.195g, 1mmol) and 4-bromomethylphenylboronic acid pinacol ester (0.296g, 1.0mmol) were dissolved in 50mL of acetonitrile, potassium carbonate (0.690g, 5.0mmol) was added, and the reaction was carried out under reflux at 85°C for 8h . After the reaction, the solvent was distilled off under reduced pressure, then dissolved in dichloromethane and methanol, and purified by column chromatography to obtain 0.357 g of near-red solid powder (87% yield). After the product is analyzed by proton nuclear magnetic resonance spectrum, its structural formula is as shown in formula (1):

[0043]

[0044]Wherein the structural formula of compound A is as shown in formula (2):

[0045]

[0046] The H NMR spectrum is as figure 1 As shown, the description of the spectrum is as follows:

[0047] 1 H NMR (400MHz, DMSO): δ7.88–7.83(m,4H),7.72–7.70(m,4H),7.48–7.47(m,2H),7.14–7.12(m,2H),5.23(s, 2H), 1.29(s,12H).MS: m / z, theoretical value: [M+H] + 412.21; Calculated: 412...

Embodiment 2

[0049] Compound A (0.195g, 1mmol) and 4-bromomethylphenylboronic acid pinacol ester (0.296g, 1.0mmol) were dissolved in 50mL of acetonitrile, sodium carbonate (0.530g, 5.0mmol) was added, and the reaction was refluxed at 40°C for 8h . After the reaction, the solvent was distilled off under reduced pressure, then dissolved with dichloromethane and methanol, and purified by column chromatography to obtain 0.243 g of near-red solid powder (yield 85.9%).

Embodiment 3

[0051] Compound A (0.195g, 1mmol) and 4-bromomethylphenylboronic acid pinacol ester (0.296g, 1.0mmol) were dissolved in 50mL of acetonitrile, potassium carbonate (0.690g, 5.0mmol) was added, and the reaction was refluxed at 85°C for 12h . After the reaction, the solvent was distilled off under reduced pressure, then dissolved in dichloromethane and methanol, and purified by column chromatography to obtain 0.318 g of near-red solid powder (yield: 77%).

[0052] Fluorescent detection of hydrogen peroxide with fluorescent probes for hydrogen peroxide:

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Abstract

The invention discloses a hydrogen peroxide fluorescent probe as well as a preparation method and application thereof. The hydrogen peroxide fluorescent probe has a chemical structural formula shown in a formula (1) shown in the specification. The preparation method of the hydrogen peroxide fluorescent probe specifically comprises the following steps: (1) preparing raw materials; (2) dissolving cyanobiphenol, 4-bromomethylphenylboronic acid pinacol ester and an alkali in a solvent, and reacting for 1-24 hours to obtain a mixed solution; and (3) separating and purifying the mixed solution to obtain the hydrogen peroxide fluorescent probe. The hydrogen peroxide fluorescent probe is applied to qualitative and quantitative determination of hydrogen peroxide in a water body and qualitative determination of hydrogen peroxide in a biological sample, has good stability and optical properties, is large in Stokes shift value, and also has the advantages of high selectivity and sensitivity, highresponse speed, wide response range and low detection limit; meanwhile, raw materials used in the preparation method are easy to obtain, and the synthesis yield is high.

Description

technical field [0001] The invention belongs to the technical field of chemical analysis and detection, and in particular relates to a hydrogen peroxide fluorescent probe and its preparation method and application. Background technique [0002] Hydrogen peroxide (H 2 o 2 ) is an important physiologically active oxygen molecule, and studies have shown that abnormal levels of hydrogen peroxide are associated with various diseases, such as inflammatory diseases, cardiovascular diseases, neurodegenerative diseases and cancer. But studies have found that abnormal levels of hydrogen peroxide are also linked to many diseases. Therefore, it is of great significance to develop a simple and reliable method to detect hydrogen peroxide for the diagnosis of related diseases and the research of pathological mechanism. [0003] Fluorescence detection based on molecular probes has the advantages of simple sample processing, low cost, simple and fast operation, etc., and has been develope...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/025C09K11/06C09K2211/1007C09K2211/1096G01N21/6428G01N21/643
Inventor 李学强梁波朱盛沛郑东晗施文黄骅
Owner HUNAN ZHONGDA CONSTR ENG TESTING TECH
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