Preparation method and application of 1-methylpiperazine rhodamine amide

A technology of rhodamine amide and methylpiperazine is applied in the field of simple preparation of rhodamine B derivative optical sensing materials, and can solve the problems of complex hydrogen ion identification and detection methods, low identification response sensitivity, poor selectivity and the like , to achieve the effect of strong reversibility and stability, fast and sensitive optical response, and low consumption of raw materials

Inactive Publication Date: 2019-09-20
ANHUI UNIVERSITY OF TECHNOLOGY
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  • Abstract
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Problems solved by technology

[0005] The purpose of the present invention is to overcome the defects of the existing identification and detection methods of hydrogen ions in organisms or in the environment, such as complex, expensive instruments, cumbersome processes, low identification response sensitivity, poor selectivity, etc., and use the basic principle of optical sensing to The three-step reaction, mild reaction conditions, cheap and easy-to-obtain raw materials, function-oriented design and synthesis of rhodamine B derivatives with good optical performance and novel structure, and the fluorescence analysis method with simple equipment is used to identify and detect with high sensitivity, specificity and selectivity Hydrogen ion

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  • Preparation method and application of 1-methylpiperazine rhodamine amide

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preparation example Construction

[0029] The present invention a kind of preparation method (as figure 1 shown), specifically comprising the following steps: firstly dissolving Rhodamine B in an appropriate amount of ethanol, adding hydrazine hydrate after stirring, heating to reflux and reducing the reaction for a certain period of time, then concentrating the solvent to obtain a yellow crude product, and then using concentrated hydrochloric acid and a certain concentration of Sodium hydroxide adjusts the acidity of the reaction medium to nearly neutral, and a large amount of precipitates are precipitated. After filtering and drying, a light pink rhodamine B hydrazide intermediate product powder is obtained; then rhodamine B hydrazide is dissolved in methylene chloride, and chloroacetyl chloride is added React with acid-binding agent triethylamine, stir rapidly under ice-salt bath, remove solvent, obtain purple solid crude product, and obtain white solid after neutral alumina passes through the column; finally...

Embodiment 1

[0032] (1) Dissolve Rhodamine B 1.2g (2.5mmol) in 30mL ethanol solvent, add 98% (mass percentage) hydrazine hydrate 2mL, heat and reflux at 80°C for 3h, concentrate the solvent, precipitate a yellow product, pump After filtering and drying, put it in a small beaker, continuously add concentrated hydrochloric acid dropwise to completely dissolve the product into a purple-red solution, then adjust the pH value of the system to about 7.0 with 40% aqueous sodium hydroxide solution, and precipitate a large amount of light pink solid, suction filter and dry Obtain light pink rhodamine B hydrazide intermediate product powder afterwards;

[0033] (2) Weigh 0.456g (1mmol) of rhodamine B hydrazide and dissolve it in 25mL of dichloromethane, add 0.4mL (2.50mmol) of chloroacetyl chloride, and add 0.5mL of triethylamine as an acid-binding agent, The reaction was rapidly stirred in an ice-salt bath for 10 h, and the solvent was evaporated to obtain a crude lavender solid product, which was ...

Embodiment 2

[0038](1) Dissolve Rhodamine B 1.2g (2.5mmol) in 30mL ethanol solvent, add 98% (mass percentage) hydrazine hydrate 2.5mL, heat and reflux at 90°C for 1.5 hours, concentrate the solvent, and precipitate a yellow product , suction filtered, dried and placed in a small beaker, continuously dropwise added concentrated hydrochloric acid to completely dissolve the product into a purple-red solution, then adjusted the pH value of the system to about 7.0 with 40% aqueous sodium hydroxide solution, a large amount of pale pink solid was precipitated, and suction filtered 1. Obtain light pink rhodamine B hydrazide intermediate product powder after drying;

[0039] (2) Weigh 0.456g (1mmol) of rhodamine B hydrazide and dissolve it in 25mL of dichloromethane, add 0.4mL (2.50mmol) of chloroacetyl chloride, and add 1.0mL of triethylamine as an acid-binding agent, The reaction was rapidly stirred in an ice-salt bath for 10 h, and the solvent was evaporated to obtain a crude lavender solid prod...

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Abstract

The invention provides a preparation method and an application of 1-methylpiperazine rhodamine amide, and belongs to the technical fields of synthesis and applications of organic materials. The preparation method concretely comprises the following steps: adding an excess amount of hydrazine hydrate to an ethanol solution of rhodamine B, heating for refluxing and reacting to obtain an initial product, and adjusting the reaction system to be neutral by using concentrated hydrochloric acid and a sodium hydroxide solution respectively to obtain a reduced pale pink intermediate rhodamine B hydrazide; dissolving the rhodamine B hydrazide in dichloromethane, and reacting the obtained dichloromethane solution of the rhodamine B hydrazide with chloroacetyl chloride under the action of an acid binding agent triethylamine to obtain a white solid; and finally dissolving the white solid in acetonitrile, and reacting the obtained solution with 1-methylpiperazine under the catalysis of potassium carbonate to prepare the 1-methylpiperazine rhodamine amide molecular probe. The synthesis method has the advantages of simplicity, low dosages of reagents, mild reaction conditions, and good water solubility of the product, and the synthesized probe has excellent selectivity, reversibility and stability in identification of hydrogen ions, and can be developed as an environmental pH optical sensor. .

Description

technical field [0001] The invention belongs to the technical field of synthesis and application of organic materials, and in particular relates to a synthesis method for easily preparing rhodamine B derivative optical sensing materials and its application. Background technique [0002] The measurement of system pH plays an important role in various fields of science and technology such as chemical process control, medical diagnosis and environmental analysis. In the determination of system pH, the electrochemical method using glass electrodes is one of the most widely used methods in laboratories today. Compared with the traditional electrochemical detection method, the optical sensing method has the advantages of small size, low cost, fast response time, strong safety, no need for reference electrode and real-time detection, which has attracted widespread attention of scientists. Therefore, in recent years, The research and application of optical pH sensors are developing...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1044C09K2211/1088G01N21/643
Inventor 吴芳辉罗祥瑞杨俊卿魏先文孙文斌
Owner ANHUI UNIVERSITY OF TECHNOLOGY
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