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Preparation method of compound (I) 4-hydroxy substituted phenyl imine type rhodamine 6G fluorescence molecule probe and purpose thereof

A technology of hydroxybenzene and p-hydroxyacetophenone, which is applied in the application field of chemical sensing technology, can solve the problems of high impedance of glass electrodes, easy damage, and large volume of glass electrodes, and achieve the effect of simple synthesis and safe preparation process

Inactive Publication Date: 2013-08-07
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Electrochemical method is a common method for measuring pH value in the early days, but many problems have been encountered in the measurement, such as the high impedance of the traditional glass electrode, easy to break, and it is not suitable for the measurement of pH in fluorine-containing solutions, etc.
Secondly, glass electrodes are not suitable for in-situ processing and analysis of samples and online detection of microenvironment and living organisms due to their large volume.

Method used

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  • Preparation method of compound (I) 4-hydroxy substituted phenyl imine type rhodamine 6G fluorescence molecule probe and purpose thereof
  • Preparation method of compound (I) 4-hydroxy substituted phenyl imine type rhodamine 6G fluorescence molecule probe and purpose thereof
  • Preparation method of compound (I) 4-hydroxy substituted phenyl imine type rhodamine 6G fluorescence molecule probe and purpose thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] compound Synthesis:

[0033] (1) Synthesis of raw material rhodamine 6G hydrazide

[0034] Dissolve 1.0 g of Rhodamine 6G in 20 mL of ethanol, add it to a 100 mL flask, add 1.6 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 0.9 g of the product with a yield of 89.5%.

[0035] (2) Synthesis of the target compound

[0036] Add 0.5 g rhodamine 6G hydrazide and 0.1 g p-hydroxyacetophenone to a 100 mL flask, add 3 mL methanol to dissolve the solid, then add 2-3 drops of glacial acetic acid dropwise, heat the mixed system to reflux until complete reaction, wait After the reaction was completed, it was lowered to room temperature, and the mixed system in the flask was poured into a beaker containing a mixtur...

Embodiment 2

[0042] compound Synthesis:

[0043] (1) Synthesis of raw material rhodamine 6G hydrazide

[0044] Dissolve 5.0 g of Rhodamine 6G in 100 mL of ethanol, add it to a 250 mL flask, add 8 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 3.9 g of the product with a yield of 82.1%.

[0045] (2) Synthesis of the target compound

[0046] Add 2.0 g of rhodamine 6G hydrazide and 0.5 g of p-hydroxyacetophenone to a 100 mL flask, add 12 mL of methanol to dissolve the solid, then add 0.2 mL of glacial acetic acid, heat the mixed system to reflux until complete reaction, after the reaction is completed Cool down to room temperature, pour the mixed system in the bottle into a beaker filled with ice-water mixture, adjust the s...

Embodiment 3

[0048] compound Synthesis:

[0049] (1) Synthesis of raw material rhodamine 6G hydrazide

[0050] Dissolve 8.0 g of rhodamine 6G in 150 mL of ethanol, add it to a 250 mL flask, add 12.8 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 6.0 g of the product with a yield of 77.3%.

[0051] (2) Synthesis of the target compound

[0052] Add 5.0 g of rhodamine 6G hydrazide and 1.3 g of p-hydroxyacetophenone to a 100 mL flask, add 30 mL of methanol to dissolve the solid, then add 0.5 mL of glacial acetic acid, heat the mixed system to reflux until complete reaction, after the reaction is completed Cool down to room temperature, pour the mixed system in the flask into a beaker filled with ice-water mixture, adjust the...

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Abstract

The invention discloses a preparation method of compound (I) 4-hydroxy substituted phenyl imine type rhodamine 6G fluorescence molecule probe and purpose thereof. The compound I has the advantages of rhodamine fluorescence dye, and simultaneously can emit strong fluorescence in the highly acid environment, and the solution color is changed from achromatic color to orange red. Therefore, the compound I has the purposes of naked eye color developing identification and fluorescence identification with high selectivity to hydrogen ion.

Description

[0001] The invention was conducted with the funding of the Tianjin Normal University Development Fund (fund number 52XK1102). Technical field [0002] The invention is the field of chemical sensing technology, involving compounds I1- (4-hydroxybenzene) amine ethyl- N’ -(Rodin Ming 6g-肼) preparation method, and the use of compound I for high-selective naked eye color recognition and fluorescent recognition probe for hydrogen ions. Background technique [0003] In physiology, pharmacy, environmental science, etc., the measurement of the pH value has very important value.Electrochemistry is a common method for measuring the pH value in the early days, but many problems encountered in measurement, such as high impedance, easily damaging traditional glass electrodes, and not suitable for measurement of pH in fluoride solution.Secondly, due to the large volume of the glass electrodes, it is not suitable for the in situ processing analysis of the sample and the online detection of micro ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64G01N21/78
Inventor 史学芳胡灵敏郭萍徐本花石倩刘丽娟刘明霞苑津平
Owner TIANJIN NORMAL UNIVERSITY
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