Hydrazine visualization fluorescent probe molecule and preparation method thereof

A fluorescent probe and molecular technology, applied in chemical instruments and methods, fluorescence/phosphorescence, material analysis through optical means, etc., to achieve stable results, simple production, and good specificity

Inactive Publication Date: 2021-08-31
XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, it is necessary to develop a fluorescent probe molecule that has the above advantages and is simple to prepare and easy to operate to meet the needs of efficient detection of hydrazine, so as to solve the shortcomings of on-site and rapid detection of hydrazine

Method used

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  • Hydrazine visualization fluorescent probe molecule and preparation method thereof
  • Hydrazine visualization fluorescent probe molecule and preparation method thereof
  • Hydrazine visualization fluorescent probe molecule and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Synthesis of fluorescent probe molecule 3-oxo-3H-spiro[isobenzofuran-1,9'-oxanthene]-3',6'-diacylbis(3-nitrobenzoate):

[0033] a, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride 2mmol, 0.384g, 4-dimethylaminopyridine 2mmol, 0.244g and 3-nitrobenzoic acid 6mmol, Mix 1.002g into a 200mL round-bottomed flask, then add 50mL of dichloromethane, stir at room temperature for 10min, and form a clear and transparent solution after completely dissolving, then add 2mmol of fluorescein, 0.664g, and stir at room temperature for 24h to stop the reaction;

[0034]b. After the reaction is cooled to room temperature, add 100 mL of dichloromethane, fully dissolve, filter to remove impurities, and then use vacuum distillation to obtain the crude product;

[0035] c. Purify the crude product obtained in step b through a silica gel column, wash with dichloromethane:ethyl acetate eluent with a volume ratio of 15:1, and then dry the eluted product to obtain a white solid for dete...

Embodiment 2

[0039] Synthesis of fluorescent probe molecule 3-oxo-3H-spiro[isobenzofuran-1,9'-oxanthene]-3',6'-diacylbis(3-cyanobenzoate):

[0040] a, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride 3mmol, 0.576g, 4-dimethylaminopyridine 3mmol, 0.366g and 3-cyanobenzoic acid 9mmol, 1. Mix 323g into a 300mL round-bottomed flask, then add 75mL of dichloromethane, stir at room temperature for 10min, after completely dissolving, it becomes a clear and transparent solution, then add 3mmol of fluorescein, 1.0g, stir at room temperature for 24h, stop the reaction;

[0041] b. After the reaction is cooled to room temperature, 150 mL of dichloromethane is added by volume ratio, fully dissolved, filtered to remove impurities, and then the crude product is obtained by distillation under reduced pressure;

[0042] c. Purify the crude product obtained in step b through a silica gel column, wash with dichloromethane:ethyl acetate eluent with a volume ratio of 20:1, and then dry the eluted pr...

Embodiment 3

[0045] Synthesis of fluorescent probe molecule 3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-3',6'-diacylbis(3-fluorobenzoate):

[0046] a, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride 2mmol, 0.384g, 4-dimethylaminopyridine 2mmol, 0.244g and 3-fluorobenzoic acid 6mmol, 1.002 g to mix, add to a 200mL round-bottomed flask, then add 50mL of dichloromethane, stir at room temperature for 10min, after completely dissolving, it becomes a clear and transparent solution, then add 2mmol of fluorescein, 0.664g, stir at room temperature for 24h, stop the reaction;

[0047] b. After the reaction is cooled to room temperature, add 100 methylene chloride by volume, fully dissolve, filter to remove impurities, and then use vacuum distillation to obtain the crude product;

[0048] c. Purify the crude product obtained in step b through a silica gel column, wash with dichloromethane:ethyl acetate eluent with a volume ratio of 15:1, and then dry the eluted product to obtain a white s...

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Abstract

The invention provides a hydrazine visualization fluorescent probe molecule and a preparation method thereof. The preparation method comprises the steps of mixing compounds of 4-dimethylaminopyridine, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 3-R-benzoic acid and fluorescein, conducting reaction completely under the room temperature condition, then adding a dichloromethane solvent to obtain a crude product; and purifying the crude product by using a forward silica gel chromatographic column to obtain a white solid fluorescent probe molecule 3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-3',6'-diyl bis(3-R benzoate) for detecting hydrazine. When hydrazine reacts with a fluorescent probe molecule ester bond, a recognition part is removed, a fluorescence emission center is separated, fluorescein with strong column green fluorescence emission is generated, and qualitative detection of hydrazine is realized through fluorescence color signal change. The method is simple in preparation process and low in cost, has excellent detection selectivity and sensitivity, can be used for rapidly and qualitatively detecting hydrazine, and has a wide application prospect.

Description

technical field [0001] The invention relates to a fluorescent probe molecule for hydrazine detection and a preparation method thereof, which belongs to the field of organic chemistry and analysis and detection, and realizes the detection of hydrazine through the change of fluorescence spectrum and spectral color. Background technique [0002] Hydrazine (N 2 h 4 ), also known as hydrazine, is a class of energetic chemical hazardous chemicals with the characteristics of being highly toxic, highly corrosive, flammable and explosive. In addition, hydrazine is also a highly polar, highly active base and strong reducing agent, and is widely used in aerospace, fuel cells, chemical industry, agricultural chemistry, pesticides, photographic chemicals, emulsifiers, dyes and other fields (ACS Sustainable Chemistry & Engineering, 2020, 8, 4457-4463, ACS Omega, 2020, 5, 28369-28374, The Journal of Organic Chemistry, 2020, 85, 12175-12186 and Analytical Chemistry, 2019, 91, 7360-7365). ...

Claims

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Application Information

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IPC IPC(8): C07D493/10C09K11/06G01N21/64
CPCC07D493/10C09K11/06G01N21/6428C09K2211/1088G01N2021/6439
Inventor 窦新存马志伟胡晓云李继广
Owner XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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