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p-N-methyl acetamidophenyl rhodamine 6G pH fluorescence molecular probe as well as preparation method and use thereof

A technology based on benzene and acetamide, applied in the application field of chemical sensing technology, can solve the problems of low sensitivity of colorimetry, high impedance of glass electrode, unsuitable pH value measurement, etc., and achieve the effect of simple synthesis and safe preparation process

Inactive Publication Date: 2013-08-14
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The sensitivity of the colorimetric method is low, and it cannot meet the detection of small pH changes in the living system, so it cannot be applied to the living system for imaging of living cells. The electrode method also encounters many problems in the measurement of pH, such as the impedance of the traditional glass electrode. High, easy to break, and not suitable for the determination of pH in fluorine-containing solutions, and there are "sodium errors" in highly alkaline environments. Compared with the above two methods, the pH fluorescent probe analysis method has good selectivity, It has the characteristics of high sensitivity, small sample size, convenience and quickness, etc. It has been widely used in analytical chemistry, especially in molecular biology, bioanalytical chemistry, cell biology, medicine and other fields.

Method used

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  • p-N-methyl acetamidophenyl rhodamine 6G pH fluorescence molecular probe as well as preparation method and use thereof
  • p-N-methyl acetamidophenyl rhodamine 6G pH fluorescence molecular probe as well as preparation method and use thereof
  • p-N-methyl acetamidophenyl rhodamine 6G pH fluorescence molecular probe as well as preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] compound Synthesis:

[0037] (1) Synthesis of raw material rhodamine 6G hydrazide

[0038] Dissolve 1.5 g of Rhodamine 6G in 30 mL of ethanol, add it to a 100 mL flask, add 2.4 mL of 80% hydrazine hydrate to the mixed system at room temperature, stir for 30 minutes, then heat the mixture to reflux, when the solution changes from scarlet to When the reaction was clear orange, the reaction was completed, cooled to room temperature, and the solvent was removed by rotary evaporation to obtain 1.3 g of the product with a yield of 87.5%.

[0039] (2) Synthesis of raw material p-acetamidoacetophenone

[0040] Add 1.0 g of p-aminoacetophenone to a 100 mL flask, add 0.7 mL of acetic anhydride and 0.3 mL of glacial acetic acid dropwise at room temperature, and heat the mixed system to reflux until complete reaction. After the mixed system is cooled to room temperature, pour the mixture into a In a beaker of ice salt, stir well, and suction filter to obtain 1.0 g of pink solid...

Embodiment 2

[0050] compound Synthesis:

[0051] (1) Synthesis of raw material rhodamine 6G hydrazide

[0052] Dissolve 6.0 g of Rhodamine 6G in 120 mL of ethanol, add it to a 250 mL flask, add 9.6 mL of 80% hydrazine hydrate to the mixed system at room temperature, stir for 30 minutes, then heat the mixture to reflux, when the solution changes from scarlet to When the reaction was clear orange, the reaction was completed, cooled to room temperature, and the solvent was removed by rotary evaporation to obtain 4.6 g of the product with a yield of 79.2%.

[0053] (2) Synthesis of raw material p-acetamidoacetophenone

[0054] Add 1.5 g of p-aminoacetophenone to a 100 mL flask, add 1.0 mL of acetic anhydride and 0.4

[0055] mL of glacial acetic acid, and the mixed system was heated to reflux until the reaction was complete. After the mixed system was cooled to room temperature, the mixture was poured into a beaker filled with ice salt, stirred thoroughly, and 1.4 g of a pink solid was obt...

Embodiment 3

[0059] compound Synthesis:

[0060] (1) Synthesis of raw material rhodamine 6G hydrazide

[0061] Dissolve 10.0 g of rhodamine 6G in 188 mL of ethanol, add it to a 250 mL flask, add 16.0 mL of 80% hydrazine hydrate to the mixed system at room temperature, stir for 30 minutes, then heat the mixture to reflux, when the solution changes from scarlet to When it was a clear orange, the reaction was complete, cooled to room temperature, and the solvent was removed by rotary evaporation to obtain 7.0 g of the product, with a yield of 72.0%.

[0062] (2) Synthesis of raw material p-acetamidoacetophenone

[0063] Add 3.0 g of p-aminoacetophenone to a 100 mL flask, add 2.1 mL of acetic anhydride and 0.75 mL of glacial acetic acid dropwise at room temperature, and heat the mixed system to reflux until complete reaction. After the mixed system is cooled to room temperature, pour the mixture into a In a beaker of ice salt, fully stirred, and suction filtered to obtain 2.7 g of pink sol...

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PUM

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Abstract

The invention discloses a compound (I) P-N-methyl acetamidophenyl rhodamine 6G pH fluorescence molecular probe as well as a preparation method and use thereof. Under the action of hydrogen ions, the rhodamine 6G lactam spiral ring in the probe molecule (I) is opened in ring from closed state, and the color of the solution is obviously changed from achromatic color to orange red with fluorescence-emission; and furthermore, fluorescent light can be given off under the action of exciting light with a certain wavelength. The compound I can be used for high-sensitivity naked eye color identification for hydrogen ions and also used as a fluorescent identifying probe.

Description

[0001] The present invention is carried out under the support of the Development Fund of Tianjin Normal University (the fund number is 52XK1102). technical field [0002] The invention belongs to the application field of chemical sensing technology, and relates to the compound 1-(4-acetamidophenyl)iminoethyl- N’ -The preparation method of (rhodamine 6G-hydrazide), and the application of compound I to naked-eye chromogenic recognition and fluorescent recognition probe with high selectivity to hydrogen ions. Background technique [0003] In industrial production, the pH value of the system has a great influence on the reaction properties of substances. In addition, in biological systems, many important physiological processes of cells and organelles are also closely related to pH, so the measurement of pH value is very important. significance. There are many methods for measuring pH, such as colorimetry, electrode method and optical sensor. The sensitivity of the colorimetri...

Claims

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Application Information

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IPC IPC(8): C07D491/107C09K11/06G01N21/25G01N21/64
Inventor 史学芳胡灵敏郭萍刘丽娟端君君徐本花夏云敏苑津平
Owner TIANJIN NORMAL UNIVERSITY
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