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Thiophenol fluorescent probe based on 7-lignocaine-3-hydroxycoumarin structure and preparation method thereof

A technology of hydroxycoumarin and diethylamino, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problem of inability to selectively distinguish thiophenol and aliphatic thiol, and detect thiophenol It takes a long time to achieve the effect of easy monitoring and control, easy separation and high purity

Inactive Publication Date: 2016-03-23
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the main problems of many thiophenol fluorescent probes are the inability to selectively distinguish thiophenol and aliphatic thiols, and the long time required for detection of thiophenol, etc.

Method used

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  • Thiophenol fluorescent probe based on 7-lignocaine-3-hydroxycoumarin structure and preparation method thereof
  • Thiophenol fluorescent probe based on 7-lignocaine-3-hydroxycoumarin structure and preparation method thereof
  • Thiophenol fluorescent probe based on 7-lignocaine-3-hydroxycoumarin structure and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0018] Example 1: Synthesis of 7-diethylamino-3-hydroxycoumarin. Dissolve 200.0mg (0.86mmol) of 7-diethylamino-3-aminocoumarin in 3mL of 1mol / L hydrochloric acid, heat up to 100°C, follow the reaction by TLC, complete the reaction in 1.5 hours, cool to room temperature, and use 25 % ammonia water was adjusted to neutrality, and a large amount of yellow solids were separated out, extracted three times with 15mL dichloromethane each time, the organic phase was dried with anhydrous sodium sulfate, filtered, the solvent was evaporated under reduced pressure, and the yellow solid was separated and purified by silica gel column chromatography. Green solid 172.7mg, yield 86%. 1 HNMR (400MHz, CDCl 3 ):δ7.21(d,J=8.4Hz,1H),6.99(s,1H),6.63(s,1H),6.56(s,1H),5.80(s,1H)3.40(q,J=6.8 Hz,4H),1.20(t,J=6.8Hz,6H). 13 CNMR (100Hz, CDCl 3 ): δ160.7, 151.3, 147.9, 135.7, 126.8, 115.4, 109.3, 97.6, 44.2, 29.2, 11.9. HRMS (ESI) (C 13 h 15 NO 3 )m / z: calculated for [M+H] + :234.1130.Found[M+H] ...

Embodiment 2

[0019] Example 2: Synthesis of 7-diethylamino-3-hydroxycoumarin. Dissolve 200.0 mg (0.86 mmol) of 7-diethylamino-3-aminocoumarin in 3 mL of hydrochloric acid with a concentration of 1.5 mol / L, heat up to 100 ° C, follow the reaction by TLC, complete the reaction in 1 hour, cool to room temperature, and use 25% ammonia water was adjusted to neutral, and a large amount of yellow solids were precipitated, extracted three times with 15mL dichloromethane each time, the organic phase was dried with anhydrous sodium sulfate, filtered, the solvent was evaporated under reduced pressure, and purified by silica gel column chromatography to obtain Yellow-green solid 184.7mg, yield 92%.

Embodiment 3

[0020] Example 3: Synthesis of 7-diethylamino-3-hydroxycoumarin. Dissolve 200.0mg (0.86mmol) of 7-diethylamino-3-aminocoumarin in 3mL of 1.5mol / L hydrochloric acid, raise the temperature to 100°C, follow the reaction by TLC, complete the reaction in 2 hours, cool to room temperature, and wash with saturated carbonic acid The sodium hydrogen solution was adjusted to be neutral, and a large amount of yellow solids were precipitated, extracted three times with 15mL dichloromethane each time, the organic phase was dried with anhydrous sodium sulfate, filtered, the solvent was evaporated under reduced pressure, and purified by silica gel column chromatography to obtain Yellow-green solid 178.7mg, yield 89%.

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Abstract

The invention discloses a thiophenol fluorescent probe based on 7-lignocaine-3-hydroxycoumarin structure and a preparation method thereof and belongs to the technical field of chemical analysis and detection. In a THF / HEPES buffering system, the probe can selectively react with thiophenol, strong fluorescent substances of 7-lignocaine-3-hydroxycoumarin are released, and the portion, where the wavelength is 493 nm, of the reaction system has a fluorescent signal. An experimental result shows that the probe can fast react with thiophenol, the detecting limit is low and is only 7.3 nM, Stokes displacement is large, and fast, qualitative and quantitative detection of thiophenol can be achieved through fluorescence enhancement responses of the probe to thiophenol. A detection method is easy to operate, high in accuracy and sensitivity and good in selectivity, and the probe has the actual application value in the environment field.

Description

technical field [0001] The invention relates to the preparation of a thiophenol fluorescent probe based on 7-diethylamino-3-hydroxycoumarin structure and its selective fluorescence detection of thiophenol, belonging to the technical field of chemical analysis and detection. Background technique [0002] Thiophenol belongs to thiol compound, which is widely used in the production of pesticides, polymer materials and pharmaceuticals, and is an important chemical raw material. However, thiophenol is extremely toxic, and its median lethal concentration to fish is 0.01mM to 0.4mM. Human exposure to thiophenol liquid or gas will cause severe damage to the central nervous system and other related systems. These include shortness of breath, muscle weakness, pulmonary edema, coma and even death. Therefore, it is very important to detect thiophenols in the environment and in biological systems. Fluorescent probe detection has the advantages of simple operation, high sensitivity, and...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D311/16G01N21/64
CPCC07D311/16C09K11/06C09K2211/1088G01N21/643
Inventor 张大同王小波
Owner QILU UNIV OF TECH