Bifunctional fluorescent probe for detecting HSO3- and hydrazine hydrates and preparation method and application of probe

A technology of fluorescent probe and hydrazine hydrate, which is applied in the field of bifunctional fluorescent probe and its preparation, and can solve the problems such as few reports of bifunctional fluorescent probe

Inactive Publication Date: 2019-08-27
NANJING FORESTRY UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In recent years, a variety of bifunctional fluorescent probes have been reported, but they can simultane...

Method used

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  • Bifunctional fluorescent probe for detecting HSO3- and hydrazine hydrates and preparation method and application of probe
  • Bifunctional fluorescent probe for detecting HSO3- and hydrazine hydrates and preparation method and application of probe
  • Bifunctional fluorescent probe for detecting HSO3- and hydrazine hydrates and preparation method and application of probe

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Experimental program
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Embodiment 1

[0031] The preparation method of 3-(4″-((2-cyano)ethylacrylate)-1′,1″-biphenyl-4′-carbonyl)nopineone fluoroboron complex, the reaction formula:

[0032]

[0033] Specific steps are as follows:

[0034] 1, the preparation of 3-(4'-bromobenzoyl) nopinone:

[0035] 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 phas...

Embodiment 2

[0043] Dissolve 3-(4″-((2-cyano)ethylacrylate)-1′,1″-biphenyl-4′-carbonyl)nopineone fluoroboron complex in PBS buffer (pH= 7.2, 10mM, 7 / 3 (v / v) ethanol / water), prepared to a concentration of 1.0×10 -6 For the solution of M, hydrazine hydrate was also dissolved in PBS buffer solution to form a concentration of 0, 1, 2, 4, 6, 8, 10, 20, 40, 60, 80, 100, 200×10 -7 M's solution. Measure the effect of different concentrations of hydrazine hydrate on 3-(4″-((2-cyano) ethyl acrylate group)-1′,1″-biphenyl-4′-carbonyl) nopinone fluoroboron complex Fluorescence spectra, such as figure 1 shown. The results show that the fluorescence intensity of the compound around 490nm is obviously weakened, and the fluorescence intensity around 550nm is obviously enhanced. It shows that 3-(4″-((2-cyano)ethylacrylate)-1′,1″-biphenyl-4′-carbonyl)nopineone fluoroboron complex can be used as a fluorescent ratiometric probe Hydrazine hydrate was tested.

Embodiment 3

[0045] Dissolve 3-(4″-((2-cyano)ethylacrylate)-1′,1″-biphenyl-4′-carbonyl)nopineone fluoroboron complex in PBS buffer (pH= 7.2, 10mM, 7 / 3 (v / v) ethanol / water), prepared to a concentration of 1.0×10 -6 For the solution of M, hydrazine hydrate was also dissolved in PBS buffer solution to form a concentration of 0, 1, 2, 4, 6, 8, 10, 20, 40, 60, 80, 100, 200×10 -7M's solution. Measure the effect of different concentrations of hydrazine hydrate on 3-(4″-((2-cyano) ethyl acrylate group)-1′,1″-biphenyl-4′-carbonyl) nopinone fluoroboron complex UV absorption spectrum, such as figure 2 shown. The results show that the ultraviolet absorption intensity of the compound around 360nm is obviously weakened, and the ultraviolet absorption intensity around 280nm is obviously enhanced. It shows that 3-(4″-((2-cyano)ethylacrylate)-1′,1″-biphenyl-4′-carbonyl)nopineone fluoroboron complex can be used as a color ratio probe Hydrazine hydrate was tested.

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Abstract

The invention discloses a bifunctional fluorescent probe for detecting HSO3- and hydrazine hydrates and a preparation method and application of the probe. The preparation method comprises the steps ofcarrying out a condensation reaction on 3-(4'-formyl-1',1'-biphenyl-4'-carbonyl) norpinone and 2-ethyl cyanoacetate to obtain 3-(4'-((2-cyano) ethyl acrylate)-1',1'-biphenyl-4'-carbonyl) norpinone; making 3-[4'-(1-cyano-2-ethoxycarbonyl)vinyl-1',1'-biphenyl-4'-carbonyl] norpinone react with boron trifluoride diethyl ether to obtain a 3-[4'-(1-cyano-2-ethoxycarbonyl)vinyl-1',1'-biphenyl-4'-carbonyl] norpinone-based fluorine-boron complex. After the 3-(4'-((2-cyano) ethyl acrylate)-1',1'-biphenyl-4'-carbonyl) nopinone fluorine-boron complex prepared by means of the method is complexed with HSO3- ions, the fluorescence color of a solution is changed from blue green to blue. After a reaction with the hydrazine hydrates, the fluorescence color of the solution is changed from blue green to yellow, and the probe can be used as a bifunctional fluorescence probe and has a good application prospect in the aspect of identifying the HSO3- ions and the hydrazine hydrates.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis and relates to a method for detecting HSO 3 - A bifunctional fluorescent probe of hydrazine hydrate and its preparation method and application. Background technique [0002] Hydrazine (NH 2 NH 2 ) and bisulfate (HSO 3 - ) as a necessary raw material in industrial production is widely used in many fields. First, NH 2 NH 2 Due to its strong reducing and nucleophilic properties, it has wide applications in chemical industry, catalysis, pharmaceuticals, aerospace and agriculture. However, NH 2 NH 2 When absorbed by the body, it can cause serious damage to the liver, lungs, kidneys and central nervous system. As a potential human carcinogen, the U.S. Environmental Protection Agency (EPA) stipulates that N 2 h 4 The threshold limit of 10ppb (0.312μM). In addition, as an antioxidant and antibacterial agent, HSO 3 - It is widely used in daily life, such as beverage, food and...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07F5/02G01N21/64G01N21/78
CPCC09K11/06C07F5/022G01N21/643G01N21/78C09K2211/1007C09K2211/1096
Inventor 杨益琴姜倩王石发徐海军王忠龙徐徐李明新王芸芸杨海燕
Owner NANJING FORESTRY UNIV
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