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Fluorescent probe molecule for detecting hydrogen peroxide and preparation method thereof

A fluorescent probe and hydrogen peroxide technology, applied in the field of fluorescent probe molecules and their preparation, to achieve the effect of low cost, fast response and fast response speed

Inactive Publication Date: 2021-08-17
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

Therefore, there is an urgent need to develop a fluorescent probe molecule that has the above advantages and is simple to prepare to meet the demand for hydrogen peroxide detection, so as to solve the problem of on-site and rapid detection of hydrogen peroxide.

Method used

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  • Fluorescent probe molecule for detecting hydrogen peroxide and preparation method thereof
  • Fluorescent probe molecule for detecting hydrogen peroxide and preparation method thereof
  • Fluorescent probe molecule for detecting hydrogen peroxide and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Fluorescent probe molecule 2',7'-dichloro-3',6'-bis((4-(4,4,5,5-tetramethyl-1,3,2-dioxolane- Synthesis of 2-yl)benzyloxy)-3H-spiro[isobenzofuran-1,9'-oxanthene]:

[0031] a. Add 1.5mmol of dichlorofluorescein, 0.6g, 4mmol of potassium carbonate, 0.56g, 6mmol of 4-bromomethylphenylboronic acid pinacol ester, 1.8g and 50mL of acetonitrile into a 100mL round-bottomed flask, at a temperature of 90°C Heat and stir to dissolve, condense and reflux overnight for 20 hours, and stop the reaction after the reaction is complete;

[0032] b. After the reaction is cooled to room temperature, add 50 mL of acetonitrile, stir well, filter to remove impurities, and obtain a crude product;

[0033] c. The crude product obtained in step b is purified by forward silica gel chromatography, the eluent is dichloromethane, and the eluted product is dried to obtain a white solid fluorescent probe molecule 2',7'-di Chloro-3',6'-bis((4-(4,4,5,5-tetramethyl-1,3,2-dioxolan-2-yl)benzyloxy)-3H- sp...

Embodiment 2

[0037] Fluorescent probe molecule 2',7'-dihydro-3',6'-bis((4-(4,4,5,5-tetramethyl-1,3,2-dioxolane- Synthesis of 2-yl)benzyloxy)-3H-spiro[isobenzofuran-1,9'-oxanthene]:

[0038] a. Add fluorescein 1.5mmol, 0.5g, potassium carbonate 4mmol, 0.56g, 4-bromomethylphenylboronic acid pinacol ester 6mmol, 1.8g and 50mL acetonitrile into a 100mL round bottom flask, heat and stir at 90°C Dissolve, condense and reflux for overnight reaction for 20 hours, and stop the reaction after the reaction is complete;

[0039] b. After the reaction is cooled to room temperature, add 50 mL of acetonitrile, stir well, filter to remove impurities, and obtain a crude product;

[0040] c, purifying the crude product obtained in step b through a forward silica gel chromatography column, the eluent is dichloromethane, and the eluted product is dried to obtain a white solid fluorescent probe molecule for detecting hydrogen peroxide;

[0041] Proton NMR data: 1 H NMR (400MHz, DMSO-d 6 )δ11.04(s,2H),7.98(...

Embodiment 3

[0043] Selective detection of hydrogen peroxide by fluorescent probe molecules:

[0044] Using the fluorescent probe molecules prepared in Example 1 to evaluate the specific detection and recognition of this type of probe molecules to hydrogen peroxide, figure 2 When adding various common interfering substances or strong oxidizing agents to the fluorescent probe, the fluorescence intensity of the test paper will change, for example adding 1mmol / L interfering substances is (Bi(NO 3 ) 3 、CoCl 2 、Cs 2 CO 3 , FeCl 3 , FeSO 4 , HgCl 2 、K 2 Cr 2 o 7 , KCl, KI, KMnO 4 , MgCl 2 、Na 2 SO 3 , NaClO 4 、NaNO 2 , NH 4 NO 3 、NiCl 2 , Pb(CH 3 CO 2 ) 2 、CH 4 N 2 S, CH 4 ON, CH 4 N 2 O or Zn(CH 3 CO 2 ) 2 ) The probe excitation wavelength is 365 nanometers, and the emission wavelength is 526 nanometers; when adding hydrogen peroxide in the fluorescent probe solution, the fluorescence intensity of the fluorescent probe solution increases sharply, and when adding va...

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Abstract

The invention discloses a fluorescent probe molecule for detecting hydrogen peroxide and a preparation method thereof. The preparation method comprises the following steps: mixing a compound 2-R-group fluorescein, potassium carbonate, 4-bromomethyl phenylboronic acid pinacol ester and acetonitrile, heating and stirring, carrying out reflux condensation reaction, and adding an acetonitrile solvent after the reaction is cooled to room temperature to obtain a crude product; and purifying the obtained crude product through a forward silica gel chromatographic column to obtain the white solid fluorescent probe molecule 2', 7'-diR-3', 6'-bis ((4-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxol-2-yl) benzyloxy)-3H-spiro[isobenzofuran-1, 9'-xanthene] for detecting hydrogen peroxide, wherein the content of hydrogen peroxide is detected through the change of fluorescence signal intensity. Due to the fact that hydrogen peroxide and probe molecules are chemically reacted to cause rearrangement elimination of boric acid ester groups, 2-R-based fluorescein with high luminous efficiency is released, and the detection specificity and sensitivity are improved; and the preparation process is simple, the cost is low, the excellent specificity and sensitivity are achieved, and the fluorescent probe molecule can be used for rapidly detecting hydrogen peroxide on site, and has a wide application prospect.

Description

technical field [0001] The invention relates to a fluorescent probe molecule for detecting hydrogen peroxide and a preparation method thereof, which belongs to the fields of organic chemistry and analysis and detection, and detects hydrogen peroxide through the change of fluorescence signal intensity. Background technique [0002] Hydrogen peroxide, also known as hydrogen peroxide, is a strong oxidizing agent widely used in fields such as industrial bleaching, electroplating, surgical disinfection and military rocket propellants. Hydrogen peroxide is involved in a variety of important human physiological processes [Journal of the American Chemical Society, 2012, 134, 1305-1315, Chemical Communications, 2013, 49, 9929-9931 and Science, 2006, 312, 1882-1883.]. Abnormal concentration of hydrogen peroxide in the human body is related to many diseases, such as Alzheimer's disease, cancer, diabetes, DNA damage, cardiovascular disease and neurodegenerative diseases [Nature, 2004, 4...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/025C09K11/06G01N21/643C09K2211/1088C09K2211/1096C09K2211/1007
Inventor 窦新存马志伟王培贤祖佰祎
Owner XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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