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Preparation and application of N-(2-hydroxy-5-chlorobenzene)ylrhodamine B hydrazide

A technology of hydrazide and chlorobenzene, which is applied in the field of easy preparation of rhodamine B derivative fluorescent sensing materials, can solve the problems of complex zinc ion identification and detection methods, low identification response sensitivity, and cumbersome processes, and achieve raw materials Less dosage, good recognition selectivity and high optical activity

Active Publication Date: 2018-10-02
ANHUI UNIVERSITY OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to overcome the existing deficiencies such as complex zinc ion recognition and detection methods in living organisms or in the environment, expensive instruments, cumbersome processes, low recognition response sensitivity, and poor selectivity. One-step reaction, mild reaction conditions, cheap and easy-to-obtain raw materials, function-oriented design and synthesis of rhodamine B derivatives with good optical properties and novel structure, and the fluorescence analysis method with simple equipment is used to identify and detect zinc ions with high sensitivity, specificity and selectivity

Method used

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  • Preparation and application of N-(2-hydroxy-5-chlorobenzene)ylrhodamine B hydrazide
  • Preparation and application of N-(2-hydroxy-5-chlorobenzene)ylrhodamine B hydrazide
  • Preparation and application of N-(2-hydroxy-5-chlorobenzene)ylrhodamine B hydrazide

Examples

Experimental program
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Effect test

Embodiment 1

[0026] (1) Dissolve 1.2g (2.5mmol) of Rhodamine B in ethanol solvent, add 2mL of 80% hydrazine hydrate, heat and reflux at 80°C for 3 hours, concentrate the solvent, and precipitate a yellow product, filter it with suction, dry it and put it in In a small beaker, continuously drop concentrated hydrochloric acid to dissolve the product completely into a purple-red solution, then adjust the pH value of the system to about 7.0 with 40% aqueous sodium hydroxide solution, and a large amount of light pink solid is precipitated. After suction filtration and drying, light pink rhodamine is obtained. B hydrazide intermediate product powder;

[0027] (2) Dissolve 0.456g (1mmol) of the intermediate product in step (1) in methanol and add 0.133g (0.8mmol) of 5-chlorosalicylaldehyde. After refluxing at 50°C for 28 hours, a white solid precipitates and cools to room temperature. Afterwards, suction filtration, washing, vacuum drying at 40°C for 12 hours, and finally recrystallization twice ...

Embodiment 2

[0029] (1) Dissolve 1.2g (2.5mmol) of rhodamine B in ethanol solvent, add 4mL of 80% hydrazine hydrate, heat and reflux at 90°C for 1 hour, concentrate the solvent, and precipitate a yellow product, filter it with suction, dry it and put it in In a small beaker, continuously drop concentrated hydrochloric acid to dissolve the product completely into a purple-red solution, then adjust the pH value of the system to about 7.0 with 40% aqueous sodium hydroxide solution, and a large amount of light pink solid is precipitated. After suction filtration and drying, light pink rhodamine is obtained. B hydrazide intermediate product powder;

[0030] (2) Dissolve 0.456g (1mmol) of the intermediate product in step (1) in methanol and add 0.199g (1.2mmol) of 5-chlorosalicylaldehyde. After refluxing at 70°C for 20 hours, a white solid precipitates and cools to room temperature. Afterwards, suction filtration, washing, vacuum drying at 50°C for 8 hours, and finally recrystallization twice wi...

Embodiment 3

[0032] (1) Dissolve 1.2g (2.5mmol) of rhodamine B in ethanol solvent, add 3mL of 80% hydrazine hydrate, heat and reflux at 85°C for 2 hours, concentrate the solvent, and precipitate a yellow product, filter it with suction, dry it and put it in In a small beaker, continuously drop concentrated hydrochloric acid to dissolve the product completely into a purple-red solution, then adjust the pH value of the system to about 7.0 with 40% aqueous sodium hydroxide solution, and a large amount of light pink solid is precipitated. After suction filtration and drying, light pink rhodamine is obtained. B hydrazide intermediate product powder;

[0033] (2) Dissolve 0.456g (1mmol) of the intermediate product in step (1) in methanol and add 0.166g (1.0mmol) of 5-chlorosalicylaldehyde. After reflux at 60°C for 24 hours, a white solid is precipitated and cooled to room temperature. Afterwards, suction filtration, washing, vacuum drying at 45°C for 10 hours, and finally recrystallization twice...

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Abstract

Belonging to the technical field of inorganic material synthesis and application, the invention provides preparation and application of N-(2-hydroxy-5-chlorobenzene)ylrhodamine B hydrazide. The invention adopts liquid-phase synthesis method. The method includes: firstly adding excess hydrazine hydrate into a rhodamine B ethanol solution, carrying out heating reflux reaction to obtain an initial product, then employing concentrated hydrochloric acid and a sodium hydroxide solution respectively to adjust the reaction system to neutral, thus obtaining a reduced intermediate product rhodamine B hydrazine; then further reacting the rhodamine B hydrazine with 5-chlorosalicylaldehyde in methanol, and conducting recrystallization to obtain N-(2-hydroxy-5-chlorobenzene)ylrhodamine B hydrazide for rapid, sensitive and highly selective recognition or even trace detection of zinc ions. The compound has the advantages of simple synthesis process, mild reaction conditions, small reagent dosage, lowmaking cost, little environmental pollution, and good optical properties and biocompatibility, and can be developed as a brand new fluorescent probe for zinc ion recognition in organisms.

Description

technical field [0001] The invention belongs to the technical field of synthesis and application of inorganic materials, and in particular relates to a synthesis method for easily preparing rhodamine B derivative fluorescent sensing materials and its application. Background technique [0002] Zinc ion is one of the essential trace elements in living organisms. It mainly exists in the brain, pancreas and sperm cells in the human body. It plays a very important physiological role in gene expression, cell apoptosis, enzyme regulation and neurotransmission. . The lack of zinc ions will lead to many diseases including nerve damage, epilepsy, temporary global cerebral ischemia, Alzheimer's disease, etc. At the same time, zinc ions are also a kind of heavy metal ions. Zinc and other industries will cause great pollution to the environment, so it is of great research significance to find methods and technologies that can quickly and non-invasively identify and evaluate the concentr...

Claims

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Application Information

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IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1088G01N21/6428
Inventor 吴芳辉杨俊卿魏先文孙文斌王晓玲
Owner ANHUI UNIVERSITY OF TECHNOLOGY
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