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Fluorescent compound and application thereof in hypochlorous acid detection

A technology of fluorescent compounds and hypochlorous acid, which is applied in the field of analysis and detection, can solve the problems of difficulty in realizing fluorescent test paper type detection, weakening of red fluorescence, and increase of blue fluorescence intensity, etc., and achieves high accuracy, easy aggregation, and simple preparation process. Effect

Inactive Publication Date: 2016-10-26
SOUTH CHINA UNIV OF TECH
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Problems solved by technology

Chinese patent CN201210528045.7 prepared diphenylselenyl derivatives based on naphthalimide. This compound reacts with hypochlorous acid to form selenium oxide. Under the irradiation of excitation light, fluorescence enhancement can occur in the wavelength range of 500nm–575nm. In this way, the fluorescence-enhanced detection of hypochlorous acid is realized; however, the detection system is easily interfered by other oxides, and the fluorescent probe has the property of aggregation-induced quenching, which makes it difficult to achieve fluorescent test paper detection
Fluorescence ratiometric detection method (for example published paper ACS Appl.Mater.Interfaces, 2016, 8, 1511–1519), synthesized a fluorescent probe based on pyrene indole derivatives, under 430nm laser irradiation, the The probe molecule emits red fluorescence at 613nm. After the addition reaction of the double bond and hypochlorous acid, the indole derivative of pyrene becomes the aldehyde derivative of pyrene, so that under the same excitation light, the 470nm The blue fluorescence intensity increased significantly, while the red fluorescence at 613nm was greatly weakened, realizing the fluorescence ratiometric detection of hypochlorous acid; however, the fluorescent probe has the property of aggregation-induced quenching, which makes it difficult to realize the fluorescent test paper detection

Method used

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  • Fluorescent compound and application thereof in hypochlorous acid detection
  • Fluorescent compound and application thereof in hypochlorous acid detection
  • Fluorescent compound and application thereof in hypochlorous acid detection

Examples

Experimental program
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Effect test

Embodiment 1

[0047] (1) 1982mg (4-hydroxy-phenyl)-phenyl-methanone (10mmol) and 2611mg (4-bromophenyl)-phenyl-methanone (10mmol) were dissolved in 120mL tetrahydrofuran, and 3923mg zinc was added under stirring Powder (60mmol), nitrogen protection, 7.40mL titanium tetrachloride (67.5mmol) was added dropwise under ice bath conditions, the ice bath was removed, first reacted at room temperature for 1 hour, then heated to reflux overnight, and the temperature was controlled at 70°C; After cooling to room temperature, it was extracted with ethyl acetate / saturated sodium bicarbonate solution, and the organic phase was dried over anhydrous sodium sulfate and filtered; the organic solvent was removed by rotary evaporation, and the resulting solid was purified by silica gel chromatography (eluent: n-hexane / dichloromethane, V / V=1:3), to obtain white solid product 4-[2-(4-bromo-phenyl)-1,2-diphenyl-vinyl]-phenol 1800mg (yield is 42.1%); the product was characterized by 1H NMR, 1H NMR (600MHz, DMSO,...

Embodiment 2

[0053] (1) 932mg (4-hydroxy-phenyl)-phenyl-methanone (4.70mmol) and 1364mg (4-bromophenyl)-phenyl-methanone (5.22mmol) were dissolved in 47mL tetrahydrofuran and added under stirring 1690mg of zinc powder (25.85mmol), under nitrogen protection, 2.83mL of titanium tetrachloride (25.85mmol) was added dropwise under ice bath conditions, removed from the ice bath, first reacted at room temperature for 0.5 hours, then heated and refluxed overnight, and controlled the temperature to 67°C; after cooling to room temperature, extract with ethyl acetate / saturated sodium bicarbonate solution, dry the organic phase with anhydrous sodium sulfate, and filter; remove the organic solvent by rotary evaporation, and the resulting solid is purified by silica gel chromatography (eluent : n-hexane / dichloromethane, V / V=1:3), to obtain white solid product 4-[2-(4-bromo-phenyl)-1,2-diphenyl-vinyl]-phenol 837mg ( Yield 41.7%).

[0054] (2) Dissolve 641mg 4-[2-(4-bromo-phenyl)-1,2-diphenyl-vinyl]-phen...

Embodiment 3

[0060] (1) 595mg (4-hydroxy-phenyl)-phenyl-methanone (3mmol) and 825mg (4-bromophenyl)-phenyl-methanone (3.16mmol) were dissolved in 34.5mL tetrahydrofuran and added under stirring 1118mg of zinc powder (17.1mmol), protected by nitrogen gas, added 2.09mL of titanium tetrachloride (19.07mmol) dropwise under ice bath conditions, removed the ice bath, first reacted at room temperature for 0.7 hours, then heated to reflux overnight, and controlled the temperature to 68°C; after cooling to room temperature, extract with ethyl acetate / saturated sodium bicarbonate solution, dry the organic phase with anhydrous sodium sulfate, filter; remove the organic solvent by rotary evaporation, and purify the obtained solid by silica gel chromatography (eluent : n-hexane / methylene chloride, V / V=1:3), to obtain white solid product 4-[2-(4-bromo-phenyl)-1,2-diphenyl-vinyl]-phenol 537mg ( Yield 41.9%).

[0061] (2) Dissolve 427mg 4-[2-(4-bromo-phenyl)-1,2-diphenyl-vinyl]-phenol (1mmol) in 6.5mL N,...

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Abstract

The invention belongs to the technical field of analysis and detection and discloses a fluorescent compound and the application thereof in hypochlorous acid detection. The fluorescent compound is 2-{3-cyan-4-[2-(4'-{2-[4-(2-hydroxy-ethyoxyl)-phenyl]-1,2-biphenyl-vinyl}-biphenyl-4-yl)-vinyl]-5,5-dimethyl-5H-furyl-2-ylidene}-malononitrile, and has a structural formula as shown in formula (1). By the adoption of the fluorescent compound, enhancement mode fluorescence detection of hypochlorous acid can be achieved, interference of external conditions can be avoided during analysis and detection, and detection precision and accuracy are high; the fluorescent compound can be prepared into test paper which is convenient to carry and store and capable of achieving qualitative testing conveniently, and fluorescence quenching occurring when traditional fluorochrome is used as a solid material is avoided. The fluorescent compound can be used for qualitative and quantitative analysis of hypochlorous acid in chemical and environmental samples as well as other samples.

Description

technical field [0001] The invention belongs to the technical field of analysis and detection, and in particular relates to a fluorescent compound and its application in the detection of hypochlorous acid. Background technique [0002] Hypochlorous acid and its conjugate base HClO / ClO - As a strong oxidant, it is used in various organic synthesis, and is also used as a disinfectant and bleaching agent to achieve antifouling of the cooling water system of power stations and disinfection of tap water and drinking water. However, when hypochlorous acid is used for disinfection of tap water and drinking water, some organic chlorine by-products (OBPs) will be produced in the water, which will cause certain harm to the human body. At the same time, if the concentration of OBPs is too high, it will also cause oxidative stress in aquatic organisms, and eventually cause genotoxicity in aquatic organisms. Although ClO - It has a certain bactericidal effect, and aquatic organisms al...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/68C09K11/06G01N21/64
CPCG01N21/6428G01N21/643C09K11/06C07D307/68C09K2211/1007C09K2211/1088
Inventor 吴水珠黄帅玲王俊武英龙曾钫
Owner SOUTH CHINA UNIV OF TECH
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