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Blue fluorescent compound and preparation method thereof

A blue fluorescence and compound technology, applied in the field of fluorescent compounds, can solve the problems of poor water solubility and photostability, high toxicity and side effects, cumbersome synthesis methods, etc., and achieve high quantum yield, simple preparation method, and high cell survival rate.

Inactive Publication Date: 2015-11-04
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the structure of these fluorescent compounds mostly does not contain active groups, such as carboxyl, amino and hydroxyl, etc., so it is difficult to use them to modify other materials. Not only the synthesis method is cumbersome, but also their water solubility and photostability are poor, and their side effects are high.

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  • Blue fluorescent compound and preparation method thereof
  • Blue fluorescent compound and preparation method thereof
  • Blue fluorescent compound and preparation method thereof

Examples

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Embodiment 1

[0026] A preparation method of blue fluorescent compound: 10mmol of anhydrous citric acid and 1mmol of cysteine ​​are added to a flask, 20mL of water is added to the flask to dissolve anhydrous citric acid and cysteine, and then The flask was placed in an oil bath, condensed and refluxed at 100°C for 12 hours; then naturally cooled to room temperature, added deionized water, left to stand at 0°C to precipitate solids, filtered, washed with water three times and placed in a vacuum drying oven Dry at 100°C to obtain a blue fluorescent compound (TPDCA).

[0027] The structure of the above-mentioned blue fluorescent compound TPDCA is determined by nuclear magnetic resonance spectroscopy, see figure 1 , the peak at 13.6ppm is the hydrogen on the two carboxyl groups, the peak at 6.5-6.6ppm is the hydrogen of the double bond on the pyridone structure, and the peaks at 3.6 and 3.9ppm are the CH on the thiazole ring structure 2 The hydrogen of 5.4-5.5ppm is the hydrogen of CH on the t...

Embodiment 2

[0030] A preparation method of a blue fluorescent compound: 10mmol of citric acid containing crystal water and 10mmol of cysteamine are added to a flask, and 30mL of N,N-dimethylformamide is added to the flask to make citric acid, Dissolve cysteamine, then place the flask in an oil bath, condense and reflux at 150°C for 1 hour; take out the above flask, cool to room temperature naturally, add deionized water, stand at 5°C to precipitate solids, filter, The resulting precipitate was washed three times with water and then dried in a vacuum oven at 95° C. to obtain a blue fluorescent compound (TPCA).

[0031] The structure of the above-mentioned blue fluorescent compound TPCA is determined by nuclear magnetic resonance spectroscopy, see figure 2 , the 13.6ppm peak is the hydrogen on the carboxyl group, the 6.5-6.6ppm peak is the hydrogen of the double bond on the pyridone structure, and the 3.5ppm peak is the CH adjacent to the sulfur atom on the thiazole ring structure 2 hydro...

Embodiment 3

[0034] A preparation method of a blue fluorescent compound: add 10mmol of anhydrous citric acid and 100mmol of cysteine ​​to a flask, then add 50mL of dimethyl sulfoxide to the flask to make anhydrous citric acid, cysteine Dissolve the acid, then place the flask in an oil bath, condense and reflux at 150°C for 7 hours; then take out the flask, cool it down to room temperature naturally, add deionized water and let it stand at 2°C to precipitate solids, filter, and the obtained The precipitate was washed three times with water and then dried in a vacuum oven at 105° C. to obtain a blue fluorescent compound (TPDCA).

[0035] The structure of the above-mentioned blue fluorescent compound TPDCA is determined by nuclear magnetic resonance spectroscopy, see figure 1 , the peak at 13.6ppm is the hydrogen on the two carboxyl groups, the peak at 6.5-6.6ppm is the hydrogen of the double bond on the pyridone structure, and the peaks at 3.6 and 3.9ppm are the CH on the thiazole ring struc...

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Abstract

The invention relates to a blue fluorescent compound and a preparation method thereof. The method includes: taking citric acid, cysteine or cysteamine as the starting raw material, adding the citric acid and cysteamine or cysteamine derivative into a solvent, then carrying out condensation reflux reaction at 100-150DEG C for 1-12; and then performing natural cooling to room temperature, adding deionized water, conducting standing at 0-5DEG C to precipitate solid, filtering and drying the solid so as to obtain the blue fluorescent compound. According to the invention, the blue fluorescent compound is prepared by means of reflux heating, contains the active group carboxyl, emits blue fluorescence under ultraviolet excitation, and has very high quantum yield over 72%. The preparation method is simple and has mild synthesis condition, thus being easy for industrialization.

Description

technical field [0001] The invention relates to the technical field of fluorescent compounds, in particular to a blue fluorescent compound and a preparation method thereof. Background technique [0002] The Spanish botanist N. Monardes recorded the fluorescence phenomenon for the first time in 1575. Since then, people have started in-depth research on the luminescence mechanism and performance of fluorescent compounds. After the fluorescent compound is excited by ultraviolet light, electricity or chemical energy, the electrons transition from the ground state to the excited state, and then release photons through radiative decay to return to the ground state and generate fluorescence. With the continuous deepening of research, fluorescence analysis methods such as simultaneous fluorescence measurement, time-resolved fluorescence measurement, and fluorescent probe technology have developed rapidly. The application of fluorescent compounds has also gradually penetrated into b...

Claims

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Application Information

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IPC IPC(8): C07D513/04C09K11/06
CPCC07D513/04C09K11/06C09K2211/1037
Inventor 杨建海石磊陈咏梅
Owner XI AN JIAOTONG UNIV
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