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Functional multi-nitrogen heterocyclic ring fluorescent probe, preparation method and application thereof

A fluorescent probe and nitrogen heterocycle technology, which is applied in the field of functionalized multiple nitrogen heterocycle fluorescent probes, can solve problems such as damage to the body, and achieve the effects of avoiding interference, good selectivity and remarkable effect.

Inactive Publication Date: 2013-12-11
HEFEI INSTITUTES OF PHYSICAL SCIENCE - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, too much hypochlorous acid will damage the body itself, so exploring an efficient and sensitive method for detecting hypochlorous acid is of great significance to the environment and organisms
However, the development of ratiometric fluorescent probes for the detection of hypochlorous acid has not been reported in the literature so far.

Method used

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  • Functional multi-nitrogen heterocyclic ring fluorescent probe, preparation method and application thereof
  • Functional multi-nitrogen heterocyclic ring fluorescent probe, preparation method and application thereof
  • Functional multi-nitrogen heterocyclic ring fluorescent probe, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1: Fluorescent Probe R 1 R 2 R 3 R 4 (Py) 2 CH 2 CHNCS (R 1 , R 2 , R 3 , R 4 Both -H) Preparation

[0038]

[0039] Place a 10mL single-necked round-bottom flask in an ice-water bath, add 1mL of dichloromethane, 1mL of ethanol, and 1.0mmol of (Py) 2 (CH 2 ) 2 NH and 1.0mmol of ammonia water, the molar amount of ammonia water is expressed as NH 3 ·H 2 O meter, stirred for 30 minutes, then added CS dropwise 2 solution, the CS 2 The solution is composed of 1.1mmol of CS 2 Dissolve in 1mL of ethanol and 1mL of dichloromethane to obtain, stir and react in an ice-water bath for 1 hour after dropping, remove the ice bath, and continue to react for 9 hours at room temperature, the whole reaction process is protected from light; after the reaction is completed, the solvent is removed by rotary evaporation Obtain the crude product, the crude product is dissolved with a very small amount of dichloromethane, then separated and purified by column chromato...

Embodiment 2

[0044] Example 2: Fluorescent Probe R 1 R 2 R 3 R 4 (Py) 2 CH 2 CHNCS (R 1 =R 4 =-H,R 2 =R 3 =-OH) preparation

[0045]

[0046] Place a 10mL single-necked round-bottom flask in an ice-water bath, add 1mL of dichloromethane, 1mL of ethanol, and 1.0mmol of (Py) 2 (CH 2 ) 2 (OH) 2 NH and 1.0mmol of ammonia water, the molar amount of ammonia water is expressed as NH 3 ·H 2 O meter, stirred for 30 minutes, then added CS dropwise 2 solution, the CS 2 The solution is composed of 1.1mmol of CS 2 Dissolve in 1mL of ethanol and 1mL of dichloromethane to obtain, stir and react in an ice-water bath for 1 hour after dropping, remove the ice bath, and continue to react for 9 hours at room temperature, the whole reaction process is protected from light; after the reaction is completed, the solvent is removed by rotary evaporation Obtain the crude product, the crude product is dissolved with a very small amount of dichloromethane, then separated and purified by column chr...

Embodiment 3

[0050] Example 3: Fluorescent Probe R 1 R 2 R 3 R 4 (Py) 2 CH 2 CHNCS (R 1 =R 4 =-H,R 2 =-OH,R 3 =-COOH) preparation

[0051]

[0052] Place a 10mL single-necked round-bottom flask in an ice-water bath, add 1mL of dichloromethane, 1mL of ethanol, and 1.0mmol of (Py) 2 (CH 2 ) 2 OHNHCOOH and 1.0mmol of ammonia water, the molar amount of ammonia water is expressed as NH 3 ·H 2 O meter, stirred for 30 minutes, then added CS dropwise 2 solution, the CS 2 The solution is composed of 1.1mmol of CS 2 Dissolve in 1mL of ethanol and 1mL of dichloromethane to obtain, stir and react in an ice-water bath for 1 hour after dropping, remove the ice bath, and continue to react for 9 hours at room temperature, the whole reaction process is protected from light; after the reaction is completed, the solvent is removed by rotary evaporation Obtain the crude product, the crude product is dissolved with a very small amount of dichloromethane, then separated and purified by column...

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Abstract

The invention discloses a functional multi-nitrogen heterocyclic ring fluorescent probe, and a preparation method and an application of the functional multi-nitrogen heterocyclic ring fluorescent probe, wherein the general structural formula of the functional multi-nitrogen heterocyclic ring fluorescent probe is shown in the specification, wherein R1, R2, R3 and R4 respectively and independently represent hydrophilic groups. The preparation method of the fluorescent probe comprises the following steps: taking bipyridine dimethylamine as a molecular skeleton, rearranging bipyridine dimethylamine after bipyridine dimethylamine is reacted with carbon disulfide to increase the molecular rigidity, and obtaining the organic probe giving out green fluorescence. The fluorescent probe is high in stability and is not easily photobleached. The fluorescent strength and the color of the probe are changed under the action of hypochlorous acid, so that the probe can be used to quantitatively and qualitatively detect the hypochlorous acid, the limit of detection is as low as 0.43 micrometer, and very high selectivity is acquired.

Description

1. Technical field [0001] The present invention relates to an organic fluorescent molecular probe, specifically a functional multi-component nitrogen heterocyclic fluorescent probe, its preparation method and its use. The fluorescent probe of the present invention can be used for the detection of hypochlorous acid or hypochlorite Qualitative and quantitative detection. 2. Background technology [0002] In recent years, fluorescence sensing technology has been increasingly applied to the analysis and detection of small biological molecules. Compared with other analysis and detection techniques, such as UV-Vis absorption spectroscopy, electrochemical methods and colorimetry, etc., fluorescence spectroscopy has its unique advantages, such as high sensitivity, high selectivity, fast response, and most importantly One point is that fluorescence spectroscopy can be used for in vivo cell imaging and real-time detection of targets. The fluorescent probes that have been developed m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D471/04G01N21/64
Inventor 王素华马芳
Owner HEFEI INSTITUTES OF PHYSICAL SCIENCE - CHINESE ACAD OF SCI
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