Coumarin thiophenol fluorescent probes and preparation method thereof

A fluorescent probe, coumarin technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve problems such as combustion and explosion, and achieve the effect of easy separation and novel structure

Active Publication Date: 2018-06-08
豆黄金食品有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When thiophenol meets with open flame, high heat or contac

Method used

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  • Coumarin thiophenol fluorescent probes and preparation method thereof
  • Coumarin thiophenol fluorescent probes and preparation method thereof
  • Coumarin thiophenol fluorescent probes and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1: Synthesis of probes. Dissolve 50.0mg (0.20 mmol) of 2,3,6,7-tetrahydro-10-hydroxy-1H,5H-quinazino(9,1-GH)coumarin in 3ml of dichloromethane, add 58.0mg (0.40 mmol) K 2 CO 3 , 37.2 mg (0.20 mmol) of 2,4-dinitrofluorobenzene, stirred at room temperature, TLC followed the reaction, the reaction was complete in 12 hours, extracted with ethyl acetate, the organic phase was dried with anhydrous sodium sulfate, filtered, evaporated under reduced pressure Solvent, separated and purified by silica gel column chromatography to obtain 62.3 dark red solids with a yield of 73.6%. 1 H NMR (400 MHz, CDCl 3 ): δ 8.86(s, 1 H), 8.32 (d, J = 6.8 Hz, 1 H), 7.53(s, 1 H), 7.10 (d, J = 9.2 Hz, 1 H), 6.88 (s, 1 H), 3.29-3.33 (m, 4 H), 2.77-2.90 (m, 4 H), 1.99-2.09 (m, 4 H). 13 C NMR (100 MHz, CDCl 3 ): Δ 157.13, 155.44,150.25, 146.30, 141.65, 138.64, 133.16, 131.39, 128.69, 125.10, 122.25,119.76, 117.64, 106.90, 49.65, 27.53, 21.25, 20.36. HRMS (ESI) (C) 13 h 15 NO 3 ) m...

Embodiment 2

[0017] Example 2: Synthesis of probes. Dissolve 50.0mg (0.20 mmol) of 2,3,6,7-tetrahydro-10-hydroxy-1H,5H-quinazino(9,1-GH)coumarin in 3mL of dichloromethane, add 0.06mL (0.40 mmol) Et 3 N, 37.2 mg (0.20 mmol) 2,4-dinitrofluorobenzene, stirred at room temperature, TLC followed the reaction, the reaction was complete in 10 hours, extracted with ethyl acetate, the organic phase was dried with anhydrous sodium sulfate, filtered, evaporated under reduced pressure The solvent was removed and purified by silica gel column chromatography to obtain 73.9 mg of dark red solid with a yield of 87.4%.

Embodiment 3

[0018] Example 3: Synthesis of probes. Dissolve 50.0mg (0.20 mmol) of 2,3,6,7-tetrahydro-10-hydroxyl-1H,5H-quinazino(9,1-GH)coumarin in 3ml of acetonitrile, add 0.09mL (0.60 mmol) Et 3 N, 37.2mg (0.20mmol) 2,4-dinitrofluorobenzene, stirred at room temperature, TLC followed the reaction, the reaction was complete in 8 hours, extracted with ethyl acetate, the organic phase was dried with anhydrous sodium sulfate, filtered, evaporated under reduced pressure The solvent was removed and purified by silica gel column chromatography to obtain 69.5 mg of reddish-brown solid with a yield of 82.2%.

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Abstract

The invention discloses fluorescent probes for specific recognition of thiophenol and a preparation method of the fluorescent probes. The probes are obtained through base catalysis of 2,3,6,7-tetrahydro-10-hydroxyl-1H,5H-quinolizino(9,1-GH)coumarin and 2,4-dinitrofluorobenzene in an organic solvent. In an acetonitrile/PBS buffer system, the probes react with thiophenol selectively to release a fluorescent substance 2,3,6,7-tetrahydro-10-hydroxyl-1H,5H-quinolizino(9,1-GH)coumarin, so that the reaction system has a strong fluorescence signal at the wavelength of 519 nm. Experiment results indicate that the probes can specifically recognize thiophenol, have the characteristics of low limit of detection (only 36 nmol/L) and large Stokes displacement (128 nm) and the like and can realize qualitative and quantitative detection of thiophenol by use of the fluorescence enhancement response to thiophenol. The probes can be obtained through chemical synthesis, the synthesis process is simple andeasy to implement, and the detection method is simple to operate, high in sensitivity and good in selectivity, so that the probes have actual application value in the biological field.

Description

technical field [0001] The invention relates to the preparation of a thiophenol fluorescent probe based on a coumarin structure and the selective fluorescence detection of thiophenol, belonging to the field of organic small molecule fluorescent probes. Background technique [0002] Thiophenol belongs to thiol compounds, a colorless liquid with a special odor, and is an important chemical raw material. However, thiophenol is highly toxic, with a median lethal dose of 0.01 mmol / L to 0.4 mmol / L for fish. Human exposure to thiophenol liquid or gas will cause serious damage to the central nervous system and other related systems, including shortness of breath, muscle weakness, nausea and vomiting, coma and even death. Thiophenol may cause combustion and explosion when exposed to open flame, high heat or contact with oxidants. Considering the harm of thiophenol to the environment and human health, it is of great significance to develop simple and effective methods for the detect...

Claims

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Application Information

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IPC IPC(8): C07D491/16C09K11/06G01N21/64
CPCC07D491/16C09K11/06C09K2211/1029C09K2211/1088G01N21/6428
Inventor 张大同潘韵霖郝雪
Owner 豆黄金食品有限公司
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