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Fluorescent probe capable of quickly detecting hydrogen sulfite ions and preparation method and application thereof

A bisulfite, fluorescent probe technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of long reaction time, low sensitivity, fluorescence color change, etc., to achieve high selectivity. Effect

Inactive Publication Date: 2019-05-10
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the reported HSO 3 - Fluorescent probes still have many deficiencies, such as: only the fluorescent color changes, the sensitivity is not high, the detection is affected by other ions, and the reaction time is long, etc.

Method used

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  • Fluorescent probe capable of quickly detecting hydrogen sulfite ions and preparation method and application thereof
  • Fluorescent probe capable of quickly detecting hydrogen sulfite ions and preparation method and application thereof
  • Fluorescent probe capable of quickly detecting hydrogen sulfite ions and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The preparation method of 3-(4″-formyl-1′, 1″-biphenyl-4′-carbonyl)nopinone-based fluoroboron complex, the reaction formula:

[0036]

[0037] Specific steps are as follows:

[0038] 1, the preparation of 3-(4'-bromobenzoyl) nopinone:

[0039] Add 0.06 mol of sodium hydride into a three-neck flask equipped with a stirrer, thermometer and reflux condenser, add 8 mL of ethylene glycol dimethyl ether under nitrogen protection, and dissolve 0.02 mol of nopinone in 9 mL of ethylene glycol dimethyl ether Slowly add into the flask, heat to reflux for 0.5h, then slowly add 0.024mol methyl 4-bromobenzoate dissolved in 9mL of ethylene glycol dimethyl ether into the flask for reflux reaction for 7-8h, track the reaction progress with thin-layer chromatography. After the reaction, the reaction solution was cooled in an ice bath, slowly added 15 mL of distilled water to hydrolyze sodium hydride, extracted 3 times with 45 mL of ethyl acetate, the combined organic phase was washed...

Embodiment 2

[0045] 3-(4″-formyl-1′, 1″-biphenyl-4′-carbonyl)nopinone-based fluoroboron complex and HSO 3 - , SO 3 2- , HS - , F - , Cl - , Br - , I - , AcO - , SCN - , NO 2 - , NO 3 - , HSO 4 - , H 2 PO 4 - , HPO 4 2- , SO 4 2- , CO 3 2- 16 different anions are dissolved in 4-hydroxyethylpiperazineethanesulfonic acid (HEPES) buffer solution (20mM, pH=7.2, 7 / 3 (v / v) ethanol / water), and the concentration is 1.0 ×10 -6 M probe solution and a concentration of 1.0 x 10 -5 Solutions of 16 different anions of M. Under the condition that the excitation wavelength is 360am, the fluorescence intensity changes in the presence of different anions are measured, such as figure 1 shown. The results showed that in HSO 3 - In the presence of ions, the maximum emission wavelength of the solution blue shifts from 520nm to 435nm. The fluorescent color of the solution changed from green to blue under the ultraviolet light, indicating that the compound is sensitive to HSO 3 - i...

Embodiment 3

[0047] Dissolve the solid 3-(4″-formyl-1′,1″-biphenyl-4′-carbonyl)nopinonylfluoroboron complex and 16 different anions in 4-hydroxyethylpiperazine In ethanesulfonic acid (HEPES) buffer solution (20mM, pH=7.2, 7 / 3 (v / v) ethanol / water), the concentration is 1.0×10 -6 M probe solution and a concentration of 1.0 x 10 -5 Solutions of 16 different anions of M. Measured HSO 3 - , SO 3 2- , HS - , F - , Cl - , Br - , I - , AcO - , SCN - , NO 2 - , NO 3- , HSO 4 - , H 2 PO 4 - , HPO 4 2- , SO 4 2- , CO 3 2- The ultraviolet absorption spectrum of the probe solution under the presence of 16 different anions, the results are as follows figure 2 shown. Probe solution in HSO 3 - In the presence of cyanide, the maximum absorption peak of the ultraviolet absorption spectrum is blue-shifted from 360nm to 260nm. It shows that the compound can be used as a color probe for HSO 3 - to test.

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Abstract

The invention discloses a fluorescent probe capable of quickly detecting hydrogen sulfite ions and a preparation method and application thereof. The preparation method includes: taking beta-pinene oxidation derivative nopinone which is one of main ingredients of natural renewable natural resource turpentine as a raw material, and allowing Claisen condensation reaction with 4-methyl bromobenzoate to obtain 3-(4'-bromobenzoyl) nopinone; allowing 3-(4'-bromobenzoyl) nopinone to be in coupling reaction with 4-formylbenzeneboronic acid to obtain 3-(4''-formyl-1', 1''-biphenyl-4'-carbonyl) nopinone;allowing 3-(4''-formyl-1', 1''-biphenyl-4'-carbonyl) nopinone to react with boron trifluoride etherate to obtain a 3-(4''-formyl-1', 1''-biphenyl-4'-carbonyl) nopinone based fluoroboron complex. Thecompound serving as a high-selectivity high-sensitivity color ratio type fluorescent probe has good application in the aspect of detecting the hydrogen sulfite ions.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis, and relates to a fluorescent probe capable of rapidly detecting bisulfite ions, a preparation method and application thereof. Background technique [0002] A large amount of combustion and use of coal, oil, natural gas, etc., lead to SO in the atmosphere 2 content is continuously increasing. As the main pollutant in the atmosphere, SO 2 Easily absorbed and converted to HSO 3 - , have a serious impact on the environment and human health. At the same time, HSO 3 - Salt is widely used as a preservative in food, wine, and medicine. In terms of epidemiological research, HSO 3 - The continuous accumulation of root ions in the human body can lead to a variety of cardiovascular diseases, such as ischemic heart disease, myocardial ischemia, and hereditary hypertension. The World Health Organization stipulates that the daily intake of bisulfite ions by the human body is 0-0.7mg / Kg,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
Inventor 杨益琴姜倩王石发徐海军王忠龙谷文徐徐李明新王芸芸
Owner NANJING FORESTRY UNIV
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