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Preparation and application of 2-methylfuran rhodamine 6G amide

A technology of methyl furan and furoyl, which is applied in the field of simple preparation of 2-methyl rhodamine 6G amide fluorescent sensing materials, and can solve the problem of low sensitivity and specific recognition of target fluorescence sensing, purification and separation Difficulties, harsh reaction conditions, etc., to achieve the effect of less raw material consumption, fast and sensitive fluorescence response, and mild reaction conditions

Inactive Publication Date: 2019-08-30
ANHUI UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to overcome the shortcomings of the existing hypochlorous acid fluorescent molecular probes, such as cumbersome synthesis process, expensive reagents, harsh reaction conditions, difficult purification and separation, low target fluorescence sensing sensitivity and specific recognition, and so on. One-step synthesis process, mild reaction conditions, higher yield and purity prepared and isolated 2-methylfuranorhodamine 6G amide compound molecular probe with excellent optical properties, so that the molecular probe can be identified with naked eyes, high sensitivity and single selectivity And detect hypochlorous acid in trace amounts

Method used

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  • Preparation and application of 2-methylfuran rhodamine 6G amide
  • Preparation and application of 2-methylfuran rhodamine 6G amide
  • Preparation and application of 2-methylfuran rhodamine 6G amide

Examples

Experimental program
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Effect test

Embodiment 1

[0031] (1) Weigh 1.2g of rhodamine 6G (2.5mmoL) and dissolve in 25mL of ethanol, add 2mL of excess hydrazine hydrate (98% by mass), heat to reflux at 80°C for 8 hours, and remove the solvent by rotary evaporation. Rhodamine 6G hydrazide intermediate was prepared by repeatedly washing with a large amount of distilled water, recrystallizing in ethanol, and vacuum drying at 25°C for 8 hours.

[0032] (2) Weigh 0.8g of rhodamine 6G hydrazide (1.7mmol) in 25mL of dichloromethane, add 0.1mL of 2-furoyl chloride (1.5mmol), and gradually add 0.5mL of triethylamine as an acid binding agent , The reaction was stirred at 25°C for 6 hours under the protection of nitrogen. After removing the solvent, neutral alumina was passed through the column (the volume ratio of ethyl acetate and petroleum ether in the mobile phase was 1:1) to obtain the light yellow solid product 2-methylfuran Rhodamine 6G amide.

Embodiment 2

[0034] (1) Weigh 1.2g of rhodamine 6G (2.5mmoL) in 30mL of ethanol, add 2mL of excess hydrazine hydrate (98% by mass), heat to reflux at 85°C for 7 hours, and remove the solvent by rotary evaporation. Rhodamine 6G hydrazide intermediate was prepared by repeatedly washing with a large amount of distilled water, recrystallizing in ethanol, and vacuum drying at 30°C for 5 hours.

[0035] (2) Weigh 0.8 g of rhodamine 6G hydrazide (1.7 mmol) in 25 mL of dichloromethane, add 0.1 mL of 2-furoyl chloride (1.5 mmol), and gradually add 1 mL of triethylamine as an acid binding agent. The reaction was stirred at 30°C for 5 hours under the protection of nitrogen. After removing the solvent, neutral alumina was passed through the column (the volume ratio of ethyl acetate and petroleum ether in the mobile phase was 1:1.25) to obtain the pale yellow solid product 2-methylfuran rhodan Ming 6G amide.

Embodiment 3

[0037] (1) Weigh 1.2g of rhodamine 6G (2.5mmoL) and dissolve in 30mL of ethanol, add 3mL of excess hydrazine hydrate (98% by mass), heat to reflux at 85°C for 6 hours, and remove the solvent by rotary evaporation. Rhodamine 6G hydrazide intermediate was obtained by repeatedly washing with a large amount of distilled water, recrystallizing in ethanol, and vacuum drying at 30°C for 6 hours.

[0038] (2) Weigh 0.8g of rhodamine 6G hydrazide (1.7mmol) in 30mL of dichloromethane, add 0.15mL of 2-furoyl chloride (2.3mmol), and gradually add 1mL of triethylamine as an acid binding agent. The reaction was stirred at 30°C for 4 hours under the protection of nitrogen. After removing the solvent, neutral alumina was passed through the column (the volume ratio of ethyl acetate and petroleum ether in the mobile phase was 1:1) to obtain the pale yellow solid product 2-methylfuran rhodan Ming 6G amide.

[0039] Example 3 is the best example.

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Abstract

The invention discloses preparation and application of 2-methylfuran rhodamine 6G amide, and belongs to the technical fields of synthesis and application of organic materials. The 2-methylfuran rhodamine 6G amide is prepared by the steps of reacting rhodamine 6G with an excess of hydrazine hydrate to prepare a rhodamine 6G hydrazide intermediate, and reacting the rhodamine 6G hydrazide intermediate with 2-furoyl chloride by using triethylamine as an acid binding agent to synthesize the pale yellow solid product. According to the preparation method provided by the invention, the 2-methylfuran rhodamine 6G amide synthesized by the method is a novel hypochlorous acid fluorescence recognition molecular probe and has a stable structure, the preparation method is simple and has mild reaction conditions, and the 2-methylfuran rhodamine 6G amide has a higher yield, good purity, a good fluorescence recognition effect on hypochlorous acid, high sensitivity, and strong selectivity and stability,can be recognized by naked eyes in a wide pH range of the system, can even be used for micro-detection of the hypochlorous acid, and is a fluorescent sensor material with important application value.

Description

Technical field [0001] The invention belongs to the technical field of organic material synthesis and application, and specifically relates to a preparation method and application for the simple preparation of 2-methylfuran rhodamine 6G amide fluorescent sensing material. Background technique [0002] Reactive oxygen species (ROS) and reactive nitrogen species (RNS) are necessary signal molecules for organisms to carry out various physiological processes. As an important biological source of ROS, hypochlorous acid (HClO) is composed of hydrogen peroxide (H2O2) and Chloride ions (Cl) are produced by the catalysis of peroxidase (MPO) in activated white blood cells. HClO in the organism plays a vital role in the host's innate immunity, effective antibacterial properties, and is closely related to the production of various biological molecules, such as protein, DNA, RNA, fatty acids and cholesterol. On the other hand, the excessive formation of HClO in the human body can easily lead...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107G01N21/64
CPCC07D491/107G01N21/643G01N21/6447
Inventor 吴芳辉罗祥瑞杨俊卿魏先文朱海威余爱民
Owner ANHUI UNIVERSITY OF TECHNOLOGY