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

A technology of methylcyclopentanal and iminomethyl, which is applied in the application field of chemical sensing technology, can solve the problems of high impedance of glass electrodes, low sensitivity of colorimetry, and can not meet the detection requirements, and achieves high sensitivity and superior spectral performance. , the effect of short response time

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

At present, there are many methods for measuring pH, such as colorimetry, metal electrode method, glass electrode method and optical sensor, etc., but there are certain defects and deficiencies, especially not suitable for the measurement of extreme pH
The sensitivity of the traditional colorimetric method is low, and it cannot be applied to the living system for imaging of living cells, and cannot meet the detection of small pH changes in the living system; the electrode method also encounters many problems in the measurement of pH, such as the most common general glass The electrode has high impedance and is easily damaged. At the same time, it is not suitable for pH detection in biological systems due to defects such as electrochemical interference and possible mechanical damage.

Method used

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  • P-N-methyl cyclopentaldehyde rhodamine 6G pH fluorescence molecular probe as well as preparation method and use thereof
  • P-N-methyl cyclopentaldehyde rhodamine 6G pH fluorescence molecular probe as well as preparation method and use thereof
  • P-N-methyl cyclopentaldehyde rhodamine 6G 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 2.0 g of Rhodamine 6G in 30 mL of absolute ethanol, add it to a 100 mL flask, add 2.8 mL of 80% hydrazine hydrate to the flask at room temperature, stir for 30 minutes, and then heat the mixed system to reflux, when the color of the solution The reaction was completed when the color changed from scarlet to clear orange; cooled to room temperature, and the solvent was removed by rotary evaporation under reduced pressure to obtain 1.7 g of the product with a yield of 88.3%.

[0036] (2) Synthesis of the target compound

[0037] Add 1.0 g of rhodamine 6G hydrazide prepared above and 0.25 g of 1-methylcyclopentaldehyde to a 100 mL flask, add 6 mL of anhydrous methanol to dissolve the solid, then add 5 drops of glacial acetic acid dropwise, and heat the mixed system Reflux to complete reaction, after the reaction is completed, drop to room temperature, pour the mixed syst...

Embodiment 2

[0043] compound Synthesis:

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

[0045] Dissolve 5.0 g of Rhodamine 6G in 100 mL of absolute 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 mixed system to reflux, when the color of the solution When it changed from scarlet to clear orange, the reaction was completed; the system was cooled to room temperature, and the solvent was removed by rotary evaporation under reduced pressure to obtain 3.8 g of the product with a yield of 78.4%.

[0046] (2) Synthesis of the target compound

[0047] Add 2.0 g of rhodamine 6G hydrazide and 0.5 g of 1-methylcyclopentaldehyde to a 100 mL flask, add 20 mL of anhydrous methanol to dissolve the solid, then add 0.2 mL of glacial acetic acid, heat the mixed system to reflux, and wait for the reaction After completion, the mixed system was lowered to room temperature, the mixed system in...

Embodiment 3

[0049] compound Synthesis:

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

[0051] Dissolve 10.0 g of Rhodamine 6G in 198 mL of absolute 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 mixed system to reflux, when the color of the solution When the color changed from scarlet to clear orange, the reaction was complete; the mixture was cooled to room temperature, and the solvent was removed by rotary evaporation under reduced pressure to obtain 6.8 g of the product, with a yield of 71.0%.

[0052] (2) Synthesis of the target compound

[0053] Add 5.0 g of rhodamine 6G hydrazide and 1.3 g of 1-methylcyclopentaldehyde to a 100 mL flask, add 40 mL of anhydrous methanol to dissolve the solid, then add 0.5 mL of glacial acetic acid, and heat the mixed system to reflux until complete reaction , down to room temperature after the completion of the reaction, pour the mi...

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PUM

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Abstract

The invention discloses a compound (I) P-N-methyl cyclopentaldehyde rhodamine 6G pH fluorescence molecular probe as well as a preparation method and use thereof. When hydrogen ions are present in the detected environment, under the action of hydrogen ions, the rhodamine 6G lactam spiral ring in the probe molecular compound (I) is opened in ring from closed state, and the color of the solution is obviously changed from achromatic color to orange red with strong fluorescence-emission. 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-(1-methylcyclopentaldehyde) iminomethyl- N’ -The preparation method of (rhodamine 6G-hydrazide), and the use of compound I in highly selective naked-eye chromogenic recognition and fluorescent probe recognition for hydrogen ions. Background technique [0003] The pH value of the system has a great influence on the progress and completion of the chemical reaction of the substance. At the same time, in the biological system, many important physiological processes of cells and organelles are also closely related to pH, so the accurate determination of pH value has great significance. very important. At present, there are many methods for measuring pH, such as colorimetry, metal electrode method, glass ...

Claims

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Application Information

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IPC IPC(8): C07D491/107C09K11/06G01N21/25G01N21/64
Inventor 史学芳苑津平郭萍胡灵敏刘丽娟徐本花端君君刘明霞姜玉靓
Owner TIANJIN NORMAL UNIVERSITY
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