Coumarin derivative-based fluorescent probe and preparation method thereof

A technology of coumarin derivatives and fluorescent probes, applied in the field of fluorescent probes, can solve the problems of expensive operation and complexity of instruments, and achieve the effect of good selectivity

Pending Publication Date: 2021-02-23
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to overcome the technical defects of expensive and complicated operation of exi

Method used

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  • Coumarin derivative-based fluorescent probe and preparation method thereof
  • Coumarin derivative-based fluorescent probe and preparation method thereof
  • Coumarin derivative-based fluorescent probe and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Weigh 1.93g of 4-(diethylamino)salicylaldehyde, 3ml of diethyl malonate, and 1ml of piperidine, dissolve in 60ml of absolute ethanol, add 2 drops of glacial acetic acid, pre-dissolve at room temperature, and heat in an oil bath , reflux, the temperature rose to 85 ° C, reacted at a constant temperature for 24 hours, cooled to room temperature, and the solvent was removed by rotary evaporation. Add 20ml of concentrated hydrochloric acid and 20ml of glacial acetic acid to the swirled solution, and react at 100°C for 6h. Cool to room temperature, adjust pH to 5 with 30% NaOH solution, stir for 1 h, filter, wash with water 3 times, and dry to obtain the crude product. The crude product was separated and purified by column chromatography to obtain 7-(diethylamino)coumarin, namely compound 1.

[0035] Weigh 2.25g compound 1, dissolve it with 15ml DMF, and dissolve 6.5ml POCl 3 Add to 6.5ml DMF, mix well, and use the dropping funnel to add POCl 3 The mixed solution with DMF...

Embodiment 2

[0038] Weigh 1.93g of 4-(diethylamino)salicylaldehyde, 3ml of diethyl malonate, and 1ml of piperidine, dissolve in 60ml of absolute ethanol, add 2 drops of glacial acetic acid, pre-dissolve at room temperature, and heat in an oil bath , reflux, the temperature rose to 85 ° C, reacted at a constant temperature for 24 hours, cooled to room temperature, and the solvent was removed by rotary evaporation. Add 20ml of concentrated hydrochloric acid and 20ml of glacial acetic acid to the swirled solution, and react at 90°C for 7h. Cool to room temperature, adjust the pH to 5 with 30% NaOH solution, stir for 1 h, filter, wash with water 3 times, and dry the crude product. The crude product was separated and purified by column chromatography to obtain 7-(diethylamino)coumarin, namely compound 1.

[0039] Weigh 2.25g compound 1, dissolve it with 15ml DMF, and dissolve 6.5ml POCl 3 Add to 6.5ml DMF, mix well, and use the dropping funnel to add POCl 3 The mixed solution with DMF was ad...

Embodiment 3

[0042] Weigh 1.93g of 4-(diethylamino)salicylaldehyde, 3ml of diethyl malonate, and 1ml of piperidine, dissolve in 60ml of absolute ethanol, add 2 drops of glacial acetic acid, pre-dissolve at room temperature, and heat in an oil bath , reflux, the temperature rose to 85 ° C, reacted at a constant temperature for 24 hours, cooled to room temperature, and the solvent was removed by rotary evaporation. Add 20ml of concentrated hydrochloric acid and 20ml of glacial acetic acid to the swirled solution, and react at 110°C for 6h. Cool to room temperature, adjust pH to 5 with 30% NaOH solution, stir for 1 h, filter, wash with water 3 times, and dry to obtain the crude product. The crude product was separated and purified by column chromatography to obtain 7-(diethylamino)coumarin, namely compound 1.

[0043] Weigh 2.25g compound 1, dissolve it with 15ml DMF, and dissolve 6.5ml POCl 3 Add to 6.5ml DMF, mix well, and use the dropping funnel to add POCl 3 The mixed solution with DMF...

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Abstract

The invention belongs to the field of fluorescent probes, and particularly relates to a coumarin derivative-based fluorescent probe and a preparation method thereof. The fluorescent probe promotes deprotection reaction, red shift occurs in ultraviolet absorption and red shift occurs in fluorescence in the presence of Hg <2+> and is remarkably enhanced, and the fluorescent probe has the characteristics of good selectivity, strong anti-interference capability, quick response and the like, is a purposeful, simple, quick and sensitive Hg <2+> specific detection reagent, and can be applied to the field of materials or sensors.

Description

technical field [0001] The application belongs to the field of fluorescent probes, in particular to a fluorescent probe based on coumarin derivatives and a preparation method thereof. Background technique [0002] Hg 2+ It is one of the environmental pollutants with strong toxicity. After being absorbed by the human body, it will cause diseases of the central nervous system, kidney and endocrine system. In addition, a large amount of inorganic mercury is released into the natural environment and converted into more toxic organic mercury, which can cause cardiovascular disease, deafness, blindness and even death in humans. Therefore, the development of fast response, high sensitivity, high selectivity to detect Hg 2+ The means are of great significance to environmental protection and human health. [0003] Fluorescent probes have important applications in the fields of environmental chemistry, analytical chemistry and life sciences. Coumarin widely exists in nature, and t...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D409/04G01N21/64
CPCC09K11/06C07D409/04G01N21/64C09K2211/1088C09K2211/1092G01N2021/6417
Inventor 段洪东黄丽
Owner QILU UNIV OF TECH
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