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9-fluorene-N'-(rhodamine 6G-hydrazide)pH fluorescence molecular probe as well as preparation method and use thereof

A technology of hydrazide and fluorenone, applied in the field of chemical sensing technology, can solve the problems of electrical interference, low sensitivity of colorimetry, damage to cells, etc., and achieve high sensitivity, safe preparation process, and simple synthesis

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 live cell imaging
As we know, the pH glass electrode method has certain limitations, for example, the measurement of cell pH will cause electrical interference or damage cells, so they are not suitable for intracellular pH and microscopic research

Method used

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  • 9-fluorene-N'-(rhodamine 6G-hydrazide)pH fluorescence molecular probe as well as preparation method and use thereof
  • 9-fluorene-N'-(rhodamine 6G-hydrazide)pH fluorescence molecular probe as well as preparation method and use thereof
  • 9-fluorene-N'-(rhodamine 6G-hydrazide)pH fluorescence molecular probe as well as preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] compound Synthesis:

[0034] (1) Synthesis of raw material rhodamine 6G hydrazide

[0035] 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 turns from scarlet to When it turned into a 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 87.6%.

[0036] (2) Synthesis of the target compound

[0037] Add 1.0 g rhodamine 6G hydrazide and 0.3 g fluorenone into a 100 mL flask, add 6 mL of methanol to dissolve the solid, then add 4-6 drops of glacial acetic acid as a catalyst, heat the mixed system to reflux until complete reaction, wait After the reaction was completed, it was down to room temperature, the mixed system in the flask was poured into a beaker filled with crushed ice, the ...

Embodiment 2

[0044] compound Synthesis:

[0045] (1) Synthesis of raw material rhodamine 6G hydrazide

[0046] 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 turns from scarlet to When it turned into a clear orange, the reaction was complete, cooled to room temperature, and the solvent was removed by rotary evaporation to obtain 4.6 g of the product with a yield of 79.1%.

[0047] (2) Synthesis of the target compound

[0048] Add 3.0 g of rhodamine 6G hydrazide and 1.0 g of fluorenone into a 100 mL flask, and add 18 mL of methanol to dissolve the solid, then add dropwise 0.3 mL of glacial acetic acid as a catalyst, heat the mixed system to reflux until complete reaction, and wait for the reaction After cooling down to room temperature, pour the mixed system in the flask into a beaker filled with crushed ic...

Embodiment 3

[0050] compound Synthesis:

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

[0052] Dissolve 10.0 g of Rhodamine 6G in 190 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 turns from scarlet to When it turned into a clear orange, the reaction was complete, cooled to room temperature, and the solvent was removed by rotary evaporation to obtain 7.1 g of the product with a yield of 72.3%.

[0053] (2) Synthesis of the target compound

[0054] Put 6.0 g of rhodamine 6G hydrazide and 2.0 g of fluorenone into a 100 mL flask, and add 36 mL of methanol to dissolve the solid, then add dropwise 0.6 mL of glacial acetic acid as a catalyst, heat the mixed system to reflux until complete reaction, and wait for After the reaction was completed, it was down to room temperature, the mixed system in the flask was poured into a beaker fi...

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Abstract

The invention discloses a 9-fluorene-N'-(rhodamine 6G-hydrazide)pH fluorescence molecular probe as well as a preparation method and use thereof. Under the action of hydrogen ion induction, a rhodamine 6G lactam spiral ring in the compound is changed into a fluorescent open ring state from a colorless closed state, and therefore, the color of the solution is changed into orange red from achromatic color with fluorescence emission; in addition, strong fluorescent light is generated under the action of exciting light with a certain wavelength. The compound I can be used for high-selectivity naked eye coloration 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 9-fluorene- 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] The conduct or completion of chemical reactions, many important physiological processes of cells and organelles are closely related to pH value, and the measurement of pH value is of great significance. There are many methods for measuring pH, such as colorimetry, electrode method and optical sensor. 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 sy...

Claims

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Application Information

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IPC IPC(8): C07D491/107G01N21/64G01N21/78
Inventor 史学芳郭萍胡灵敏刘丽娟石倩端君君徐本花王小琴苑津平
Owner TIANJIN NORMAL UNIVERSITY
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