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Mono-sulfo squarylium dye fluorescence probe for detecting mercury ions and preparation method thereof

A technology of monothiosquaric acid and fluorescent probes, which is applied in the direction of azo dyes, organic dyes, fluorescence/phosphorescence, etc., to achieve the effect of specific detection

Inactive Publication Date: 2013-10-02
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the design of fluorescent probes with excellent performance in all aspects and the ability to detect mercury ions at low concentrations is still a great challenge.

Method used

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  • Mono-sulfo squarylium dye fluorescence probe for detecting mercury ions and preparation method thereof
  • Mono-sulfo squarylium dye fluorescence probe for detecting mercury ions and preparation method thereof
  • Mono-sulfo squarylium dye fluorescence probe for detecting mercury ions and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The monothiosquaric acid dye general formula shown in the general formula (wherein R=-(CH 2 ) n -CH 3 , n=3)

[0033] Add 1,3-bis-[4-(N,N-di-n-butylamino)-2-hydroxyphenyl]-2,4-cyclobutenedione (166 mg, 0.32 mmol) into a 100 mL three-necked flask , Lawson's reagent (233 mg, 0.58 mmol), and 35 mL of anhydrous toluene, heated to reflux for 4 h under nitrogen protection. The solvent was distilled off under reduced pressure, purified by silica gel column chromatography, the eluent was petroleum ether: ethyl acetate (20:1, v / v), and about 37 mg of green solid was obtained, the yield was about 22%, and the melting point was 186-188° c. FTIR (KBr): ν max 2955, 1682, 1614, 1397, 1345, 1285, 1216, 1186, 1109, 910, 889, 802, 773, 718 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ): δ 0.97 (t, J = 7.3 Hz, 12H), 1.37 (dq, J = 14.7, 7.4 Hz, 8H), 1.70-1.58 (m, 8H), 3.44-3.32 (m, 8H), 6.10 (dd, J = 4.1, 2.4 Hz, 2H), 6.41-6.28 (m, 2H), 8.17 (d, J = 9.3 Hz, 0.6H), 8.94 (d, J = 9.4 ...

Embodiment 2

[0035] The monothiosquaric acid dye general formula shown in the general formula (wherein R=-(CH 2 ) n -CH 3 , n=1) for the preparation of

[0036] Add 1,3-bis-[4-(N,N-diethylamino)-2-hydroxyphenyl]-2,4-cyclobutenedione (82 mg, 0.20 mmol) into a 50 mL three-necked flask, Lawson's reagent (162 mg, 0.40 mmol), and 30 mL of anhydrous toluene, in N 2 Heated to reflux for 1.5 h under protection. TLC traced the disappearance of the reaction raw material point, and the solvent was distilled off under reduced pressure, then the residue was washed with petroleum ether to remove soluble impurities, and purified by silica gel column chromatography, the eluent was petroleum ether: ethyl acetate (10:1, v / v) , about 56 mg of green solid was obtained, the yield was about 66%, and the melting point was 260-262 °C. FTIR (KBr): νmax 2955, 2931, 1679, 1601, 1387, 1333, 1293, 1272, 1238, 1210, 1181, 1142, 1074, 1009, 959, 857, 805, 779, 713 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ): δ 1.28 (t, J...

Embodiment 3

[0038] Squaric acid dyes have strong absorption and high-efficiency fluorescence emission in the near-infrared, making them widely used as a superior squarylium dye probe general formula (wherein R=-(CH 2 ) n -CH 3 , n=3) The specific recognition of mercury ions based on chemical reactions makes it a good mercury ion probe. figure 1 and figure 2 The general formula of the squarylium dye probe is given respectively (wherein R=-(CH 2 ) n -CH 3, n=3) The response to different metal ions in ethanol / HEPES (70:30, v / v) buffer system with pH 7.2, the presence of mercury ions will cause obvious shifts in absorption and fluorescence spectra, fluorescence enhancement, Realize the detection of mercury ions. Based on the qualitative detection of mercury ions, the quantitative test of mercury ions is realized. The experiment gives the fluorescence change curve of mercury titration image 3 , it can be seen from the titration curve that the detection of mercury ions has good linea...

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Abstract

The invention discloses a mono-sulfo squarylium dye fluorescence probe for detecting mercury ions and a preparation method thereof as well as application thereof. The preparation method comprises the following steps of: proportionally mixing oxo squarylium essence and a Lawesson's reagent, dissolving the mixture in methylbenzene, performing backflow reaction for 1.5-4 hours under the protection of inert gas after the mixture is dissolved, cooling the reaction mixture to room temperature, decompressing and distilling the reaction mixture to remove a solvent and obtain a rough product; and performing silica gel column chromatography separation on the rough product to obtain the mono-sulfo squarylium dye fluorescence probe. The mono-sulfo squarylium dye fluorescence probe provided by the invention is high in stability and can quickly, sensitively and specially detect low-concentration mercury ions; a synthesis method is simple; and the production cost is low.

Description

technical field [0001] The invention belongs to the technical field of chemical analysis and testing, and in particular relates to a monothiosquaric acid dye fluorescent probe for detecting mercury ions and its preparation method and application. Background technique [0002] Mercury is recognized as a toxic element in nature. Due to the abuse of heavy metals, mercury pollution greatly threatens the natural environment and human water sources. Elemental mercury and mercury ions can be converted into methylmercury by aquatic microorganisms after being discharged into the environment. Methylmercury is enriched in organisms through the food chain, and after entering the human body, it can cause severe nausea, vomiting, abdominal pain, and kidney function damage, which is extremely harmful. Therefore, the detection of mercury ions is of great significance. The U.S. Environmental Protection Agency (U.S. Environmental Protection Agency) stipulates that the upper limit of mercury...

Claims

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Application Information

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IPC IPC(8): C09K11/06C09B57/00G01N21/64
Inventor 傅南雁
Owner FUZHOU UNIV
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