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Fluorescent probe for detecting hypochlorous acid, preparation method and applications thereof

A fluorescent probe and reaction technology, used in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of the selectivity and sensitivity of fluorescent probes that need to be improved, and achieve high sensitivity, good selectivity, and good The effect of the response

Inactive Publication Date: 2019-11-29
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In view of this, the present invention provides a fluorescent probe and its preparation method and application, which are used to solve the problem that the selectivity and sensitivity of the existing fluorescent probes for detecting hypochlorous acid need to be improved

Method used

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  • Fluorescent probe for detecting hypochlorous acid, preparation method and applications thereof
  • Fluorescent probe for detecting hypochlorous acid, preparation method and applications thereof
  • Fluorescent probe for detecting hypochlorous acid, preparation method and applications thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0058] This embodiment carries out the preparation of compound TPE-Et

[0059] Weigh the compound TPE-Br namely 1-(4-bromophenyl)-1,2,2-triphenylethylene (822mg, 2.0mmol) and 4-ethoxycarbonylphenylboronic acid (427mg, 2.2mmol) into the magnetic In the 100mL reaction eggplant flask with a stirrer, evacuate and fill with argon gas three times. The mixture of tetrahydrofuran (30 mL), ethanol (7.5 mL) and water (7.5 mL) deoxygenated by argon bubbling was introduced into the reaction eggplant bottle through a vacuum tube, and the third reaction was carried out under reflux at 110 ° C overnight under an argon atmosphere. TLC detects the degree of reaction. After the third reaction is complete, the organic solvent in the reaction solution is distilled off under reduced pressure, and the remaining reaction solution is extracted with ethyl acetate solution, the organic phases are combined and washed three times with aqueous sodium bicarbonate solution (10%) and saturated brine, and th...

Embodiment 2

[0062] Preparation of Compound TPE-COOH

[0063] The compound TPE-Et (480 mg, 1.0 mmol) and sodium hydroxide (120 mg, 3.0 mmol) prepared in Example 1 were weighed and placed in a 50 mL reaction eggplant bottle containing a magnetic stir bar. The mixture of tetrahydrofuran (10 mL) and water (10 mL) deoxygenated by argon bubbling was introduced into the reaction flask through a vacuum tube, and the fourth reaction was carried out under reflux at 90° C. overnight under an argon atmosphere. A large amount of solids were precipitated in the reaction solution, and the reaction degree was detected by TLC. After the fourth reaction was completed, the reaction solution was suction-filtered to obtain a solid, and then purified by column chromatography (the eluent was dichloromethane and petroleum ether at a volume ratio of 1:1) to obtain a white solid product, namely the compound TPE-COOH ( 360 mg), the purity was 97%, and the yield was 80%.

[0064] see figure 2 , is the proton nuc...

Embodiment 3

[0066] Preparation of compound RhoN

[0067] Weigh Rhodamine B (1329mg, 3.0mmol) into a 250mL reaction eggplant bottle containing a magnetic stirrer, add absolute ethanol (50mL) to dissolve. Add hydrazine hydrate (10mL) to the reaction solution, reflux overnight at 90°C, detect the degree of reaction by TLC, until the reaction is complete, remove the solvent by rotary evaporation under reduced pressure, and then purify by column chromatography (the eluent is a volume ratio of 20: 1 of dichloromethane and petroleum ether) to obtain a light red solid product, compound RhoN (600mg), with a purity of 98% and a yield of 43%.

[0068] see image 3 , is the hydrogen nuclear magnetic resonance spectrum of the compound RhoN prepared in Example 3 of the present invention. NMR data of compound RhoN: 1 H NMR (400MHz, CDCl 3 )δ=7.93(m,1H),7.45(m,2H),7.10(m,1H),6.46(d,J=8.8Hz,2H),6.42(d,J=2.4Hz,2H),6.29( dd,J=2.5,8.8Hz,2H),3.61(s,2H),3.34(q,J=7.0Hz,8H),1.17(t,J=7.0Hz,12H).

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Abstract

The invention belongs to the technical field of small organic molecule fluorescent probes, particularly relates to a fluorescent probe for detecting hypochlorous acid, a preparation method and applications thereof, and provides a fluorescent probe, which has a structure represented by a formula (I). According to the present invention, the fluorescent probe has strong selectivity on hypochlorous acid, and can generate strong fluorescence response after being reacted with hypochlorous acid; when the fluorescence probe with a concentration of 5 [mu]M reacts with hypochlorous acid with a concentration of 0-150 [mu]M, the fluorescence response is enhanced along with the increase of the concentration of hypochlorous acid; and the fluorescence probe has advantages of high sensitivity, good selectivity and good response to hypochlorous acid.

Description

technical field [0001] The invention belongs to the technical field of small organic molecule fluorescent probes, and in particular relates to a fluorescent probe for detecting hypochlorous acid and a preparation method and application thereof. Background technique [0002] Reactive oxygen species (Reactive oxygen species, ROS) is a general term for a series of chemically highly active compounds and free radicals, including oxygen free radicals and peroxides. Hypochlorous acid (HClO / ClO - ) is one of the reactive oxygen species, and is widely used in anti-virus cleaning products on food surfaces and water, and also plays an important role in the human immune system. However, excessive hypochlorous acid will not only cause damage to food and water quality and produce peculiar smell, but also cause neurasthenia, cardiovascular disease, arthritis and kidney disease, and even cause cancer. [0003] The current methods for detecting hypochlorous acid mainly include iodometric m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D491/107G01N21/64
CPCC07D491/107C09K11/06C09K2211/1007C09K2211/1029C09K2211/1088G01N21/643
Inventor 李泽君段琴雅郑观生蒋银张华堂
Owner GUANGDONG UNIV OF TECH
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