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A ratiometric bifunctional fluorescent probe based on coumarin dye and its synthesis and application

A technology of coumarin dye and fluorescent probe, which is applied in the field of base coumarin dye ratio bifunctional fluorescent probe and its synthesis and application, can solve the problem of limited probe application range, low fluorescence quantum yield, and reaction time Long and other problems, to achieve the effects of efficient identification and measurement, efficient quantitative identification, and high sensitivity

Active Publication Date: 2020-11-03
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But at the same time, the related shortcomings of previous probes have gradually emerged, such as high detection limit, long reaction time, poor selectivity and ion competition, low fluorescence quantum yield, etc., thus limiting The relevant range of applications for these probes

Method used

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  • A ratiometric bifunctional fluorescent probe based on coumarin dye and its synthesis and application
  • A ratiometric bifunctional fluorescent probe based on coumarin dye and its synthesis and application
  • A ratiometric bifunctional fluorescent probe based on coumarin dye and its synthesis and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] (1) Synthesis of intermediate compound 1

[0057] Add 10.0g (56.8mmol) 7-hydroxy-4-methylcoumarin and 18.4g (130nmol) urotropine to a 250mL three-necked round-bottomed flask, then add 80mL of glacial acetic acid, dissolve it by ultrasonic, and keep the temperature of the reaction solution Reflux and stir at 90°C for 6 hours, then add 20 mL of hydrochloric acid dropwise with a dropper, continue to reflux and stir at the same temperature for 50 minutes, then cool the reaction solution to room temperature, slowly add 100 mL of ice water, and extract three times with ether (3×100 mL) , dried the organic phase with anhydrous sodium sulfate, and rotary evaporated under reduced pressure to obtain a crude product, which was purified by a column with an eluent (petroleum ether / dichloromethane=10 / 1) to obtain a light yellow solid.

[0058] (2) Synthesis of probes

[0059] Weigh 326mg (1.6mmol) of compound 1 and 216mg (2mmol) of diaminomaleonitrile, dissolve them in 30mL of ethan...

Embodiment 2

[0061] (1) Synthesis of intermediate compound 1

[0062] Add 8g of 7-hydroxy-4-methylcoumarin and 10g of urotropine to a 250mL three-necked round-bottomed flask, then add 60mL of glacial acetic acid, dissolve it with ultrasonic waves, keep the temperature of the reaction solution at 90°C and reflux for 6 hours, then use Add 20mL of hydrochloric acid dropwise through the dropper, continue to reflux and stir at the same temperature for 50 minutes, then cool the reaction solution to room temperature, slowly add 100mL of ice water, extract three times with ether (3×100mL), and dry the organic phase with anhydrous sodium sulfate , and rotary evaporation under reduced pressure to obtain a crude product, which was purified through a column with an eluent (petroleum ether / dichloromethane=10 / 1) to obtain a light yellow solid.

[0063] (2) Synthesis of probes

[0064] Weigh 300mg of compound 1 and 200mg of diaminomaleonitrile, dissolve them in 25mL of ethanol / water solution, add 4 drop...

Embodiment 3

[0066] (1) Synthesis of intermediate compound 1

[0067] Add 5.0g (28.4mmol) 7-hydroxy-4-methylcoumarin and 9.2g (65nmol) urotropine to a 250mL three-necked round-bottomed flask, then add 40mL of glacial acetic acid, dissolve it by ultrasonic, and keep the temperature of the reaction solution Reflux and stir at 90°C for 6 hours, then add 20 mL of hydrochloric acid dropwise with a dropper, continue to reflux and stir at the same temperature for 50 minutes, then cool the reaction solution to room temperature, slowly add 100 mL of ice water, and extract three times with ether (3×100 mL) , the organic phase was dried with anhydrous sodium sulfate, and the crude product was obtained by rotary evaporation under reduced pressure, and the eluent (petroleum ether / dichloromethane=10 / 1) was purified by column to obtain a light yellow solid, that is, compound 1 was 0.84 mg, the yield 14.5%. H NMR spectrum see figure 1 .

[0068] Compound 1 1 H NMR picture as figure 1 Shown: 1 H NMR ...

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Abstract

The invention belongs to the technical field of preparation and application of compounds, and particularly relates to a coumarin dye-based ratio-type bi-functional fluorescent probe, as well as synthesis and application of same. In the invention, for the first time, a new-type coumarin fluorescent ratio-type probe is synthesized. The method includes the steps of: 1) dissolving 7-hydroxy-4-methyl coumarin and urotropine in glacial acetic acid, performing a reaction, adding concentrated hydrochloric acid to the mixture so that the mixture is reacted therewith; 2) performing purification and separation by column chromatography to obtain a product, coumaric aldehyde; 3) dissolving the coumaric aldehyde and diamino maleonitrile in acetonitrile, dropwise adding a less amount of concentrated hydrochloric acid, stirring the mixture at room temperature, and performing separation and purification to obtain a final target product. The ion probe can effectively and quickly recognize copper and hypochloric acid, is high in selectivity and ionic competitiveness, and can be used for recognition of related actual water samples.

Description

technical field [0001] This experiment belongs to the technical field of compound differentiation and application, and specifically relates to a ratiometric bifunctional fluorescent probe based on coumarin dyes and its synthesis and application. Background technique [0002] As an important component of reactive oxygen species (ROS) in organisms, hypochlorous acid is an antibacterial agent in the natural defense system, which can destroy invading pathogens and bacteria, but excessive hypochlorous acid can cause tissue damage and a series of diseases , such as arthritis, cardiovascular disease, arteriosclerosis, kidney disease and cancer, etc. Hypochlorous acid is also a strong oxidant in life, such as household bleaching powder, disinfectants, antibacterial agents, and the concentration of hypochlorous acid also plays a vital role in daily life. Therefore, efficient and sensitive real-time detection of hypochlorous acid Development is also crucial. [0003] Copper is the t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/18C07D311/16C09K11/06G01N21/64
Inventor 唐勇李媛媛唐帅王赟韩娟李春梅夏晋晨倪良
Owner JIANGSU UNIV
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