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A squaraine probe based on silver ion recognition and its preparation method and application
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A technology of squaraine and silver ions, which is applied in the field of squaraine probes based on silver ion recognition and its preparation, can solve the problems of high cost and long detection time, and achieve high sensitivity, high reaction yield, and post-treatment simple effect
Active Publication Date: 2020-06-30
CHANGZHOU UNIV
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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 years has the characteristics of simple detection, high precision, and fast response, which meets the needs of development and becomes the first choice for detecting ions. method
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Embodiment 1
[0022] (1) Compound 1 (N-(4-nitrophenyl) diethanolamine, 1.13g, 5mmol) and p-toluenesulfonyl chloride (TsCl) (1.9g, 10mmol) were reacted in a mixture of tetrahydrofuran (THF) and water Compound 2 (p-toluenesulfonyl derivative of compound 1) was obtained, which was separated and purified by column chromatography to obtain 2.0 g with a yield of 74.5%;
[0023] (2) Compound 2 (2g, 3.7mmol) was slowly added dropwise to methyl thioglycolate (0.8g, 7.4mmol) and cesium carbonate (Cs 2 CO 3 , 0.26g, 0.74mmol) in anhydrous N, N-dimethylformamide (DMF), 60 ° C reflux reaction for 2 days, separated and purified by column chromatography to obtain compound 3 (ethylsulfanyl- Methyl acetate derivative) 1.2g, yield 80%;
[0024] (3) Using Pb / C (0.06g, 5%) as a catalyst and hydrazine hydrate (0.45ml, 7.5mmol) as a reducing agent, compound 3 (1.2g, 3.0mmol) was reacted in an ethanol solvent at 50°C for 2 hours, After drying under reduced pressure and suction, separation and purification by c...
Embodiment 2
[0031](1) Compound 1 (N-(4-nitrophenyl) diethanolamine, 3.2g, 14mmol) and p-toluenesulfonyl chloride (TsCl) (5.3g, 28mmol) were reacted in a mixture of tetrahydrofuran (THF) and water Compound 2 (the p-toluenesulfonyl derivative of compound 1) was separated and purified by column chromatography to obtain 5.4 g, with a yield of 71.3%;
[0032] (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), 60 ° C reflux reaction for 3 days, separated and purified by column chromatography to obtain compound 3 (ethylsulfanyl-acetic acid of compound 1 Methyl ester derivative) 2.62g, yield 65.2%;
[0033] (3) Using Pb / C (0.18g, 5%) as a catalyst and hydrazine hydrate (1ml, 8.2mmol) as a reducing agent, compound 3 (2.6g, 6.8mmol) was reacted at 50°C in an ethanol solvent for 3 hours. It was dried by suction filtration under reduced pressure, separated and puri...
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Abstract
The invention belongs to the field of chemical analysis testing, and particularly relates to a squaraine essence probe based on silver ion recognition as well as a preparation method and application thereof. A mixture of compound 5, benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (PyBop) and N,N-diisopropylethylamine (DIPEA) is stirred in dichloromethane at room temperature. After a period of time, a previously prepared compound 4 with a thioether and an ester group is added, stirring is carried out for reaction, suction filtration separation is carried out, and a finished product is obtained. The squaraine essence compound obtained by the invention has excellent optical properties and ion selectivity, and is favorable for 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 squaraine probe based on silver ion recognition, 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 has been reported that si...
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