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Rhodamine 6GpH fluorescent molecular probe containing biphenyl group as well as preparation method and application thereof

A technology of biphenyl and butyryl biphenyl is applied in the application field of chemical sensing technology, which can solve many problems and achieve the effect of high pH response sensitivity and narrow pH response range.

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

However, among the reported pH fluorescent molecular probes, there are not many probes that can be used to detect hydrogen ions in strongly acidic solutions.

Method used

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  • Rhodamine 6GpH fluorescent molecular probe containing biphenyl group as well as preparation method and application thereof
  • Rhodamine 6GpH fluorescent molecular probe containing biphenyl group as well as preparation method and application thereof
  • Rhodamine 6GpH fluorescent molecular probe containing biphenyl group as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] compound Synthesis

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

[0034] Add 2.0 g of Rhodamine 6G into a 100 mL flask, then add 20 mL of ethanol to dissolve the solid, add 3.2 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 color, the reaction was complete, cooled to room temperature, rotary evaporated, and the solvent was removed to obtain 1.7 g of the product with a yield of 87.5%.

[0035] (2) Synthesis of the target compound

[0036] Add 1.0 g of rhodamine 6G hydrazide and 0.4 g of butyrylbiphenyl into a 100 mL flask, then add 6 mL of methanol to dissolve the solid, then add dropwise 0.1 mL of glacial acetic acid as a catalyst, 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 po...

Embodiment 2

[0043] compound Synthesis:

[0044] (1) Synthesis of raw material rhodamine 6G hydrazide

[0045] Add 5.0 g of Rhodamine 6G into a 250 mL flask, then add 100 mL of ethanol to dissolve the solid, 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 turns from scarlet 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 3.9 g of the product with a yield of 81.6%.

[0046] (2) Synthesis of the target compound

[0047] Add 2.5 g of rhodamine 6G hydrazide and 1.1 g of butyrylbiphenyl into a 100 mL flask, then add 15 mL of methanol to dissolve the solid, then add 0.25 mL of glacial acetic acid as a catalyst, 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 bottle was poured into a ...

Embodiment 3

[0049] compound Synthesis:

[0050] (1) Synthesis of raw material rhodamine 6G hydrazide

[0051] Add 10.0 g of rhodamine 6G into a 500 mL flask, then add 200 mL of ethanol to dissolve the solid, add 16 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 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 7.0 g of the product with a yield of 72.8%.

[0052] (2) Synthesis of the target compound

[0053] Add 5.0 g of rhodamine 6G hydrazide and 2.2 g of butyrylbiphenyl into a 100 mL flask, add 30 mL of methanol to dissolve the solid, then add 0.5 mL of glacial acetic acid as a catalyst, heat the mixed system to reflux until complete reaction, wait After the reaction was completed, it was lowered to room temperature, the mixed system in the flask was poured into a beaker fi...

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Abstract

The invention discloses a compound (I), namely a rhodamine 6GpH fluorescent molecular probe containing a biphenyl group, as well as a preparation method and application thereof. According to the preparation method, rhodamine 6G and hydrazine hydrate react to prepare rhodamine 6G hydrazide, and a condensation reaction is carried out on the rhodamine 6G hydrazide and butyryl biphenyl to prepare the compound I. The compound has excellent optical property, fluorescence intensity is obviously enhanced when reacting with hydrogen ions, and the compound can be used for detecting the hydrogen ions in a solution.

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-(biphenyl)iminobutyl- N’ -(rhodamine 6G-hydrazide) and its preparation method and the use of naked-eye chromogenic recognition and fluorescent recognition probes with high selectivity for hydrogen ions. Background technique [0003] The progress or completion of chemical reactions, many important physiological processes of cells and organelles are closely related to the pH value of the system. Therefore, the determination of pH value is of great significance, and its testing methods mainly include spectroscopic method, electrode method and indicator method. Fluorescence spectroscopy is a detection method based on optical signals, which has the advantages of high sensitivity, high selectivity, fast r...

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 史学芳胡灵敏郭萍刘丽娟端君君徐本花夏云敏苑津平
Owner TIANJIN NORMAL UNIVERSITY
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