Probe based on 1-and-3-symmetric squarine recognizing silver ions as well as preparation method and application thereof

A silver ion and probe technology, applied in the field of squaraine probe and its preparation, can solve the problems of high cost and long detection time, and achieve the effects of high sensitivity, high reaction yield and good selectivity

Active Publication Date: 2019-02-15
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods require the use of large instruments, which are expensive and take a long time to detect. However, the rapid development of fluorescent probes in recent yea...

Method used

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  • Probe based on 1-and-3-symmetric squarine recognizing silver ions as well as preparation method and application thereof
  • Probe based on 1-and-3-symmetric squarine recognizing silver ions as well as preparation method and application thereof
  • Probe based on 1-and-3-symmetric squarine recognizing silver ions as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] (1) Fully disperse compound 1 (N-(4-nitrophenyl)diethanolamine, 1.13g, 5mmol) and p-toluenesulfonyl chloride (TsCl) (1.9g, 10mmol) in 5ml of tetrahydrofuran (THF) and 5ml In a mixture of water and reaction at room temperature for 2 h to obtain compound 2 (p-toluenesulfonyl derivative of compound 1), which was separated and purified by column chromatography to obtain 2.0 g with a yield of 74.5%;

[0028] (2) Compound 2 (2g, 3.7mmol) was added dropwise to methyl thioglycolate (0.8g, 7.4mmol) and cesium carbonate (Cs 2 CO 3 , 0.26g, 0.74mmol) of anhydrous N,N-dimethylformamide (DMF), wherein the amount of anhydrous N,N-dimethylformamide is 15ml, and reacted at a reaction temperature of 60°C for 2 days , separated and purified by column chromatography to obtain 1.2 g of compound 3 (ethylsulfanyl-methyl acetate derivative of compound 1), with a yield of 80%;

[0029] (3) Using Pb / C (0.06g, 5%) as a catalyst, hydrazine hydrate (0.45ml, 7.5mmol) as a reducing agent, compound...

Embodiment 2

[0036] (1) Compound 1 (N-(4-nitrophenyl)diethanolamine (3.2g, 14mmol) and p-toluenesulfonyl chloride (TsCl) (5.3g, 28mmol) were dissolved in 10ml of tetrahydrofuran (THF) and 10ml of water The mixture was reacted at room temperature for 4 h to obtain compound 2 (the p-toluenesulfonyl derivative of compound 1) which was separated and purified by column chromatography to obtain 5.4 g with a yield of 71.3%;

[0037] (2) Compound 2 (5.4g, 10mmol) was slowly added dropwise to methyl thioglycolate (2.16g, 20mmol) and cesium carbonate (Cs 2 CO 3 , 1.1g, 2mmol) of anhydrous N,N-dimethylformamide (DMF), wherein the amount of anhydrous N,N-dimethylformamide is 25ml, reflux at 60°C for 3 days, and pass through the column Chromatographic separation and purification yielded 2.62 g of compound 3 (ethylsulfanyl-methyl acetate derivative of compound 1), with a yield of 65.2%;

[0038] (3) Using Pb / C (0.18g, 5%) as a catalyst, hydrazine hydrate (1ml, 8.2mmol) as a reducing agent, compound 3 ...

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Abstract

The invention belongs to the field of chemical analysis tests, and more particularly relates to a probe based on 1-and-3-symmetric squarine recognizing silver ions as well as a preparation method andapplication thereof. The preparation method comprises the steps detailed as below: firstly, N-(4-nitrophenyl)iminobisetnanol and paratoluensulfonyl chloride are taken as monomers for preparing a compound 2; secondly, the compound 2 and methyl thioglycolate are used for preparing a compound 3; thirdly, the compound 3 is reduced by hydrazine hydrate for preparing a compound 4 with sulfur ether and ester groups; fourthly, the compound 4 and a compound 5 are stirred in the mixed solution of methylbenzene and n-butyl alcohol at 110 DEG C for reflux reaction, and the final product is obtained by filtration and separation. The squarine compound obtained by the invention has excellent optical performance and ionic selectivity, thereby facilitating the detection of silver ions.

Description

technical field [0001] The invention belongs to the field of chemical analysis and testing, and in particular relates to a 1,3-position symmetric squaraine probe based on identifying silver ions, a preparation method and application thereof. Background technique [0002] Heavy metal pollution has received increasing attention due to its adverse effects on the environment and human health. Heavy metals are non-biodegradable and tend to accumulate in living organisms, and many heavy metal ions are known to be toxic or carcinogenic. Among all heavy metal ions, silver ions are released into the environment in large quantities through industrial waste and waste gas every year, and a large amount of silver ions cause serious environmental pollution, further affecting food and agriculture. As one of the most important bioactive cations, silver ions exhibit excellent antibacterial activity in the low concentration range, but are toxic to the human body in high concentrations. It h...

Claims

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Application Information

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IPC IPC(8): C07C323/52C07C319/20C09K11/06G01N21/31G01N21/64
CPCC07C303/28C07C319/14C07C319/20C07C323/52C07C2601/04C09K11/06C09K2211/1007C09K2211/1014G01N21/31G01N21/6428G01N2021/6432C07C309/73
Inventor 刘晓骞王鑫王建浩丁淑敏李佳雯张紫薇姚静陈逸群
Owner CHANGZHOU UNIV
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