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Benzoxazinone thiophenol fluorescent probe and preparation method thereof

A benzoxazinone and fluorescent probe technology, which is applied in the field of analysis and detection, can solve the problems of limiting practical application and long time required for detection, and achieves the effects of good fluorescence performance, low detection limit, and easy separation and purification.

Inactive Publication Date: 2016-02-24
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

包括:WeiJiang,et.al.AHighlySelectiveFluorescentProbeforThiophenols,Angew.Chem.2007,119,8597-8600;DnyaneshwarKand,et.al.BODIPYBasedColorimetricFluorescentProbeforSelectiveThiophenolDetection:TheoreticalandExperimentalStudies,Analyst,2012,137,3921-3924;ZhengWang,et.al.Reaction- BasedFluorescentProbeforSelectiveDiscriminationofThiophenolsoverAliphaticthiolsandItsApplicationinWaterSamples, Anal.Chem.2012,84,4915-4920, etc., but due to the long time required for the detection of thiophenols by these probes, its practical application is greatly limited

Method used

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  • Benzoxazinone thiophenol fluorescent probe and preparation method thereof
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  • Benzoxazinone thiophenol fluorescent probe and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Synthesis of Fluorescent Probe Compounds Based on Benzoxazinones and Thiophenols

[0029] In a 50mL single-necked flask, 7-hydroxy-3-methylbenzoxazinone (90mg, 0.6mmol), 2,4-dinitrobenzenesulfonyl chloride (149mg, 0.6mmol) and triethylamine ( 0.25mL, 1.8mmol) was dissolved in 5mL of dry tetrahydrofuran, stirred at room temperature for 2h, the solvent was distilled off under reduced pressure, the resulting residue was dissolved in dichloromethane, washed three times with 50mL of water, and the organic phase was dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain a crude product, which was separated through a silica gel (200-300 mesh) column with dichloromethane / ethyl acetate=3 / 1 to obtain a yellow solid with a yield of 71%.

[0030] Wherein, 7-hydroxyl-3-methylbenzoxazinone can be according to literature D.R.Shridhar, B.Lal, N.K.Vaidya, K.K.Bhopale and H.N.Tripathi, Synthesis & biological activity of some 3-[2-(heteroaryl)-...

Embodiment 2

[0033] Synthesis of Fluorescent Probe Compounds Based on Benzoxazinones and Thiophenols

[0034] In a 50mL single-necked flask, 7-hydroxy-3-methylbenzoxazinone (90mg, 0.6mmol), 2,4-dinitrobenzenesulfonyl chloride (149mg, 0.6mmol) and triethylamine ( 0.25mL, 1.8mmol) was dissolved in 5mL of dry tetrahydrofuran, stirred at room temperature for 6h, the solvent was distilled off under reduced pressure, the resulting residue was dissolved in 50mL of dichloromethane, then washed three times with 50mL of water, and the organic phase was dried with anhydrous sodium sulfate , The solvent was distilled off under reduced pressure to obtain a crude product, which was separated through a silica gel (200-300 mesh) column with dichloromethane / ethyl acetate=3 / 1 to obtain a yellow solid with a yield of 66%.

Embodiment 3

[0036] Synthesis of Fluorescent Probe Compounds Based on Benzoxazinones and Thiophenols

[0037] In a 50mL single-necked flask, 7-hydroxy-3-methylbenzoxazinone (90mg, 0.6mmol), 2,4-dinitrobenzenesulfonyl chloride (224mg, 0.9mmol) and triethylamine ( 0.25mL, 1.8mmol) was dissolved in 5mL of dry tetrahydrofuran, stirred at room temperature for 2h, the solvent was distilled off under reduced pressure, the residue was dissolved in 50mL of dichloromethane, washed three times with 50mL of water, and the organic phase was dried with anhydrous sodium sulfate , The solvent was distilled off under reduced pressure to obtain a crude product, which was separated through a silica gel (200-300 mesh) column with dichloromethane / ethyl acetate=3 / 1 to obtain a yellow solid with a yield of 60%.

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Abstract

The invention discloses a benzoxazinone thiophenol fluorescent probe and a preparation method thereof, and belongs to the technical field of analysis and detection. The benzoxazinone thiophenol fluorescent probe has a favorable fluorescent property, can selectively recognize thiophenol in a buffer solution, is quick in response, low in detection limit (only 24 nM), large in Stokes displacement, enhanced in fluorescence, and high in selectivity and anti-interference capability, and can qualitatively or quantitatively analyze thiophenol in real time, thereby being applicable to thiophenol detection in the watery environment.

Description

technical field [0001] The invention relates to the technical field of analysis and detection, in particular to a benzoxazinone-based thiophenol fluorescent probe and a preparation method thereof. Background technique [0002] Thiol compounds are an important class of molecules in biological systems and chemical sciences. Aliphatic hydrocarbon sulfhydryl compounds such as cysteine, homocysteine ​​and glutathione widely exist in biological systems, and they participate in many biochemical activities in living systems. However, thiophenol, an aromatic hydrocarbon mercapto compound, is a highly toxic pollutant. Long-term exposure to thiophenol in water or air will cause a series of serious health hazards, including damage to the central nervous system, rapid heart rate, Muscle atrophy, paralysis of the lower limbs, coma and even death. Although thiophenol has the above hazards, it is widely used in chemical synthesis, especially in the preparation of pesticides and pharmaceut...

Claims

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Application Information

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IPC IPC(8): C07D265/36G01N21/64C09K11/06
CPCC07D265/36C09K11/06C09K2211/1007C09K2211/1033G01N21/64
Inventor 张大同安瑞冰
Owner QILU UNIV OF TECH
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