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A guanine-based squaraine probe and its preparation method and application

A technology of guanine and probe, which is applied in the field of guanine-based squarylium probe and its preparation, can solve the problem of poor selectivity of ion-selective electrode method, low sensitivity of oscillographic polarography, and low sensitivity of refractory elements. Advanced problems, to achieve the effect of easy control of reaction conditions, high sensitivity and good selectivity

Active Publication Date: 2019-07-26
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, atomic absorption spectrometry cannot analyze multiple elements at the same time, and its sensitivity to insoluble elements is not high, and its precision is worse than that of spectrophotometry
The ion selective electrode method has poor selectivity and has strict requirements on the pH of the solution
The sensitivity of oscillographic polarography is not high, and the lower limit of detection can only reach 5-10mol / L

Method used

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  • A guanine-based squaraine probe and its preparation method and application
  • A guanine-based squaraine probe and its preparation method and application
  • A guanine-based squaraine probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] (1) Dissolve Intermediate 1 (0.1903g, 0.6mmol) and Intermediate 2 (0.1806g, 0.6mmol) in a mixed solution of 15mL n-butanol and 15mL toluene, reflux at 110°C for 12 hours under nitrogen, and remove As a solvent, use a developing solvent of dichloromethane and methanol (volume ratio 10:1) to pass through a silica gel column to obtain 0.19 g of intermediate 3 as a blue solid.

[0024] (2) Intermediate 3 (0.0630g, 0.1mmol) obtained in step (1) and 2-amino-1,7-dihydro-6H-purin-6-one (0.0333g, 0.2mmol) were dissolved in 4 -Dimethylaminopyridine (0.0252g, 0.2mmol) was stirred in a dichloromethane solution at room temperature for 1 hour, then dicyclohexylcarbodiimide (0.0315g, 0.15mmol) was added to continue the reaction for 27 hours, and the solvent was removed under reduced pressure to obtain The blue solid was separated and purified by thin-layer chromatography (volume ratio of developer: methylene chloride: methanol = 25:1) to obtain 0.0606 g of the final product.

[0025]...

Embodiment 2

[0030] (1) Dissolve Intermediate 1 (0.3806g, 1.2mmol) and Intermediate 2 (0.3612g, 1.2mmol) in a mixed solution of 30mL n-butanol and 30mL toluene, reflux at 110°C for 12 hours under nitrogen, and remove The solvent was passed through a silica gel column with a developing solvent of dichloromethane and methanol (volume ratio = 10:1), and spin-dried to obtain 0.38 g of intermediate 3 as a blue solid.

[0031] (2) Compound 3 (0.1260g, 0.2mmol) obtained in step (1) and 2-amino-1,7-dihydro-6H-purin-6-one (0.0666g, 0.4mmol) were dissolved in 4- A dichloromethane solution of dimethylaminopyridine (0.0504g, 0.4mmol) was stirred at room temperature for 1 hour, and then dicyclohexylcarbodiimide (0.0630g, 0.3mmol) was added to continue the reaction for 27 hours. Color solid, thin-layer chromatography (volume ratio of developer: dichloromethane: methanol = 25:1) separation and purification to obtain the final product 0.1209g.

Embodiment 3

[0033] (1) Dissolve Intermediate 1 (0.3806g, 1.2mmol) and Intermediate 2 (0.3612g, 1.2mmol) in a mixed solution of 30mL n-butanol and 30mL toluene, reflux at 120°C for 13 hours under nitrogen, and remove The solvent was passed through a silica gel column with a developing solvent of dichloromethane and methanol (volume ratio = 10:1), and spin-dried to obtain 0.41 g of intermediate 3 as a blue solid.

[0034] (2) Compound 3 (0.2520g, 0.4mmol) obtained in step (1) and 2-amino-1,7-dihydro-6H-purin-6-one (0.1332g, 0.8mmol) were dissolved in 4- A dichloromethane solution of dimethylaminopyridine (0.1008g, 0.8mmol) was stirred at room temperature for 1 hour, and then dicyclohexylcarbodiimide (0.1260g, 0.6mmol) was added to continue the reaction for 30 hours. A color solid was separated and purified by thin-layer chromatography (volume ratio of developer: methylene chloride: methanol = 25:1) to obtain 0.2365 g of the final product.

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Abstract

The invention belongs to the field of chemical analysis and testing and specifically relates to a guanine-based squarylium probe and a preparation method and application thereof. The preparation method comprises the following steps: a benzomethylindole hemisquaraine compound and 5-carboxyl-2,3,3-trimethyl-1-octyl-3H-indole undergo heating refluxing under the protection of nitrogen in a mixed solvent of n-butanol and toluene; and then the product reacts with N,N'-dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) at normal temperature, and the obtained crude product undergoes thin-layer chromatographic separation to obtain the final product. The squarylium probe has excellent optical performance and ion selectivity and is beneficial to detection of cadmium ions.

Description

technical field [0001] The invention belongs to the field of chemical analysis and testing, and in particular relates to a guanine-based squarylium probe and a preparation method and application thereof. Background technique [0002] Cadmium is not an essential element for the human body, excessive intake of cadmium ions will cause poisoning. In nature, cadmium compounds have different toxicity, and cadmium oxide, cadmium chloride, and cadmium sulfate are highly toxic. Globally, 22,000 tons of cadmium enters the soil every year and enters the human body through the food chain. The average dose of cadmium poisoning to humans is 100 mg. The symptoms of acute poisoning are mainly nausea, salivation, vomiting, abdominal pain, and diarrhea, which in turn cause symptoms of central nervous system poisoning. Severe cases may die due to collapse. After the environment is polluted by cadmium, cadmium can be enriched in organisms. Therefore, it is necessary to detect cadmium ions in...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D473/18C09K11/06G01N21/64
CPCC07D473/18C09K11/06C09K2211/1029C09K2211/1044G01N21/6428
Inventor 刘晓骞姚胡银李娜王鑫闵婕周苏林晨
Owner CHANGZHOU UNIV
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