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Ratiometric fluorescent probe for detection of hydrogen sulfide and preparation method of ratio-dependent fluorescent probe

A fluorescent probe and ratiometric technology, applied in the field of analysis and detection, can solve problems such as being susceptible to interference and difficult to guarantee detection accuracy, and achieve the effect of easy aggregation

Active Publication Date: 2015-01-07
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the current conventional fluorescence methods for detecting hydrogen sulfide are mainly fluorescence-enhanced or fluorescence-quenched, and these methods are susceptible to interference (such as excitation light intensity, sample concentration, fluorescence-enhancing impurities or quenchers present in the sample, etc.), Therefore, it is difficult to guarantee the accuracy of detection

Method used

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  • Ratiometric fluorescent probe for detection of hydrogen sulfide and preparation method of ratio-dependent fluorescent probe
  • Ratiometric fluorescent probe for detection of hydrogen sulfide and preparation method of ratio-dependent fluorescent probe
  • Ratiometric fluorescent probe for detection of hydrogen sulfide and preparation method of ratio-dependent fluorescent probe

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: Preparation process 1 of probe compound TPE-NAP-N3

[0042] 1) 1305mg of 4-bromo-1,8-naphthalic anhydride (4.71mmol) was dissolved in 108mL of ethanol, and 317mg of 2-aminoethanol (5.19mmol) was slowly added dropwise under nitrogen protection. Under stirring, the The mixed solution was heated to reflux; after cooling to room temperature, the precipitate was filtered and collected, and the precipitate was recrystallized with ethanol to obtain 1254 mg of white solid 6-bromo-2-(2-hydroxyethyl)-benzisoquinoline-dione (83.2% yield). By H NMR spectroscopy ( figure 2 ) to characterize the product, 1 H NMR (400MHz, DMSO-d 6 ,δppm):8.48-8.50(d,1H),8.44-8.46(d,1H),8.24-8.26(d,1H),8.13-8.15(d,1H),7.92-7.96(t,1H),4.80 -4.83(t,1H), 4.11-4.13(t,2H), 3.62-3.65(t,2H). Among them, 8.48ppm, 8.44ppm, 8.24ppm, 8.13ppm and 7.92ppm correspond to the characteristic peaks of protons on the naphthalene ring, 4.81ppm corresponds to the characteristic peaks of hydroxyl protons...

Embodiment 2

[0049] Embodiment 2: Preparation process 2 of probe compound TPE-NAP-N3

[0050] 1) 2610mg of 4-bromo-1,8-naphthalic anhydride (9.42mmol) was dissolved in 188mL of ethanol, and 692mg of 2-aminoethanol (11.34mmol) was slowly added dropwise under nitrogen protection. Under stirring, the The mixed solution was heated to reflux; after cooling to room temperature, the precipitate was filtered and collected, and the precipitate was recrystallized with ethanol to obtain 2500 mg of white solid 6-bromo-2-(2-hydroxyethyl)-benzisoquinoline-dione (82.9% yield).

[0051] Dissolve 480mg of the above white solid (1.5mmol) and 975mg of sodium azide (15mmol) in 18mL of N,N-dimethylformamide, heat the solution to 110°C with stirring and keep it for 9 hours; cool to room temperature , adding 60 mL of deionized water, and then extracting with 300 mL of ethyl acetate. Collect the organic phase, wash the organic phase with brine, dry with 150 mg of anhydrous magnesium sulfate, and filter; the org...

Embodiment 3

[0058] Embodiment 3: Preparation process 3 of probe compound TPE-NAP-N3

[0059] 1) 870mg of 4-bromo-1,8-naphthalic anhydride (3.14mmol) was dissolved in 67mL of ethanol, and 220mg of 2-aminoethanol (3.61mmol) was slowly added dropwise under nitrogen protection. Under stirring, the The mixed solution was heated to reflux; after cooling to room temperature, the precipitate was collected by filtration, and the precipitate was recrystallized from ethanol to obtain 839 mg of white solid 6-bromo-2-(2-hydroxyethyl)-benzisoquinoline-dione (83.5% yield).

[0060] Dissolve 160mg of the above white solid (0.5mmol) and 325mg of sodium azide (5.5mmol) in 5.5mL of N,N-dimethylformamide, and heat the solution to 100°C under stirring conditions and keep it for 8 hours; cool After reaching room temperature, 30 mL of deionized water was added, followed by extraction with 200 mL of ethyl acetate. Collect the organic phase, wash the organic phase with brine, dry with 100 mg of anhydrous magnes...

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Abstract

The invention discloses a ratiometric fluorescent probe for detection of hydrogen sulfide and a preparation method of the ratiometric fluorescent probe. A compound of the probe is 2-(6-azido-1,3-dioxo-benzoisoquinolinyl)ethyl 2-(4-((4-(1,2,2-triphenylvinyl)phenoxy)methyl)-1,2,3-triazolyl)ethyl)succinate. During the preparation, 4-bromo-1,8-naphthalic anhydride is reacted with 2-aminoethanol to obtain a solid, namely, 6-bromo-2-(2-hydroxyethyl)-benzoisoquinoline-dione, the product is reacted with sodium azide to obtain a solid, namely, 6-azido-2-(2-hydroxyethyl)-benzoisoquinoline-dione; and then 6-azido-2-(2-hydroxyethyl)-benzoisoquinoline-dione is subjected to a series of reaction to obtain the solid probe compound. The probe compound is composed of hydrophobic tetraphenylvinyl and hydrophilic receptor units containing azide group and can be used for quantitative analysis of hydrogen sulfide in chemical, biological, environmental and other samples.

Description

technical field [0001] The invention relates to a fluorescent probe compound, in particular to a fluorescent probe for hydrogen sulfide detection and a preparation method thereof, belonging to the technical field of analysis and detection. Background technique [0002] Hydrogen sulfide is a flammable acidic gas, easily soluble in water. When the concentration is low, it has a foul smell like rotten eggs; when the concentration is high, it has no smell, because high concentration hydrogen sulfide can paralyze the olfactory nerve; it is an acute Highly toxic substance, inhalation of a small amount of high-concentration hydrogen sulfide can be fatal in a short period of time, and long-term exposure to hydrogen sulfide gas can anesthetize the human olfactory nervous system. Hydrogen sulfide occurs naturally in crude oil, natural gas, volcanic gas and hot springs, and it can also be produced during the breakdown of organic matter by bacteria. Hydrogen sulfide also exists in a va...

Claims

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Application Information

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IPC IPC(8): C09K11/06G01N21/64C07D401/12
Inventor 吴水珠武英龙曾钫
Owner SOUTH CHINA UNIV OF TECH
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