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A 1,3-position symmetrical squarylium probe based on amidoquinoline and its preparation method and application

A technology based on amides and quinolines, applied in squaraine dyes, chemical instruments and methods, and analysis by chemically reacting materials, can solve the problems of high cost of analysis, and achieve good selectivity and easy reaction conditions. Effects with simple control and synthesis methods

Active Publication Date: 2019-06-04
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these detection methods generally require complex multi-step sample preparation and sophisticated experimental instruments, so the analysis cost is relatively expensive

Method used

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  • A 1,3-position symmetrical squarylium probe based on amidoquinoline and its preparation method and application
  • A 1,3-position symmetrical squarylium probe based on amidoquinoline and its preparation method and application
  • A 1,3-position symmetrical squarylium probe based on amidoquinoline and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] (1) Dissolve 2-chloroacetyl chloride (0.102g, 0.9mmol) in 5mL of anhydrous CH 2 Cl 2 , then the solution was added dropwise to 30 mL of dry CH 2 Cl 2 The solution was stirred in an ice bath. After stirring at room temperature for 2 hours, the solvent was removed under reduced pressure, and by the method of column chromatography, the volume of eluent CH 2 Cl 2 :MeOH=100:1, 2-chloro-N-(quinolin-8-yl)acetamide (0.15g) was obtained as light yellow solid.

[0026] (2) Combine 2-chloro-N-(quinolin-8-yl)acetamide (0.12g, 0.545mmol) obtained in step (1) with p-phenylenediamine (0.06g, 0.55mmol), N,N -Diisopropylethylamine (DIPEA) 0.5mL, and potassium iodide (0.1g, 0.55mmol) were added to 10mL methanol solution, stirred and refluxed under nitrogen atmosphere, the mixture was cooled to room temperature, the solvent was removed under reduced pressure, and the analysis method, the volume of eluent CH 2 Cl 2 :MeOH=50:1, a yellow oil was obtained.

[0027] (3) Dissolve the y...

Embodiment 2

[0031] (1) Dissolve 2-chloroacetyl chloride (0.2 g, 1.8 mmol) in 5 mL of anhydrous CH 2 Cl 2 , then the solution was added dropwise to 30 mL of anhydrous CH 2 Cl 2 The solution was stirred in an ice bath. After stirring at room temperature for 2 hours, the solvent was removed under reduced pressure, and by the method of column chromatography, the volume of eluent CH 2 Cl 2 :MeOH=100:1, 2-chloro-N-(quinolin-8-yl)acetamide (0.2g) was obtained as light yellow solid.

[0032] (2) 2-chloro-N-(quinolin-8-yl)acetamide (0.15g, 0.68mmol) obtained in step (1) was mixed with p-phenylenediamine (0.075g, 0.68mmol), N,N -Diisopropylethylamine (DIPEA) 0.65mL, and potassium iodide (0.25g, 0.68mmol) were added to 10mL methanol solution, stirred and refluxed under nitrogen atmosphere, by column chromatography, the volume of eluent CH 2 Cl 2:MeOH=50:1, a yellow oil was obtained.

[0033] (3) Dissolve the yellow oil (0.15g, 0.49mmol) and squarylium (0.0285g, 0.25mmol) obtained in step (2)...

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Abstract

The invention belongs to the field of chemical analysis and testing and particularly relates to a preparation method and an application of a 1,3-position symmetric squarylium cyanine probe based on carboxamidoquinoline. Firstly, a mixture of 8-aminoquinoline and 2-chloroacetyl chloride is subjected to ice-bath stirring in a dichloromethane solvent, a product and p-phenylenediamine are subjected to reflux in a methanol solvent, then 3,4-diethoxy-3-cyclobutene-1,2-dione and a product are subjected to reflux reaction in toluene and n-butyl alcohol, and a final product is obtained through separation and purification. The obtained squarylium cyanine compound has excellent ionic selectivity and facilitates silver ion detection.

Description

technical field [0001] The invention belongs to the field of chemical analysis and testing, and in particular relates to a preparation method and application of a 1,3-position symmetrical squaraine dye probe of amidoquinoline. Background technique [0002] Silver ions are released into the environment at high concentrations from industrial wastes and emissions every year, and the release of a large amount of silver ions has caused serious environmental pollution, further affecting food and agriculture. As one of the most important bioactive cations, silver ions show excellent antimicrobial activity in the low concentration range, while high concentrations of silver ions are toxic to the human body. According to reports, the concentration of silver ions in water is higher than 0.9uM and will be harmful to humans. Excessive intake of silver ions poses risks to human health, including brain damage and disruption of the immune system. [0003] Designing and synthesizing chemic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/40C09B57/00G01N21/31G01N21/78
CPCC07D215/40C09B57/007G01N21/31G01N21/78
Inventor 刘晓骞李娜王建浩
Owner CHANGZHOU UNIV