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Highlight and high-purity water solubility fluorescent molecules and preparing method thereof

A fluorescent molecule and water-soluble technology, applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., can solve the problems of high price, achieve low price, low biological toxicity, and facilitate the effect of modification and coupling

Inactive Publication Date: 2015-07-15
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But they are very expensive, about 1,000 yuan per milligram

Method used

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  • Highlight and high-purity water solubility fluorescent molecules and preparing method thereof
  • Highlight and high-purity water solubility fluorescent molecules and preparing method thereof
  • Highlight and high-purity water solubility fluorescent molecules and preparing method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Weigh 0.192 g (1 mmol) of citric acid solid powder and dissolve it in 10 mL of deionized water, add 67 μL (1 mmol) of ethylenediamine into the aqueous citric acid solution, and stir evenly with a glass rod. The above solution was transferred to a 20 mL polytetrafluoroethylene-lined stainless steel reaction kettle, the lid of the kettle was tightened, and the reaction was carried out at 140° C. for 6 hours. After the reaction is completed, the reaction kettle is naturally cooled to room temperature to obtain a fluorescent aqueous solution.

[0040] The obtained fluorescent aqueous solution was separated by column chromatography, and the developer was removed by rotary evaporation to obtain IPCA solid. The developer used is a mixed solution of methanol and ethyl acetate, and the volume content of methanol in the mixed solution is 50% to 100% (100% methanol content means that methanol alone can be used as a developer). If the proportion of methanol is low (volume ratio le...

Embodiment 2

[0048] Weigh 0.192 g (1 mmol) of citric acid solid powder and dissolve it in 10 mL of deionized water, add 67 μL (1 mmol) of ethylenediamine into the citric acid solution, and stir evenly with a glass rod. The liquid was transferred to a 20mL polytetrafluoroethylene-lined stainless steel reaction kettle, the lid of the kettle was tightened, and the reaction was carried out at 140°C for 6 hours. After the reaction is completed, the reaction kettle is naturally cooled to room temperature to obtain a fluorescent aqueous solution. Ethyl acetate was selected as the extractant, and the fluorescent aqueous solution was extracted, and the extractant was removed by rotary evaporation to obtain IPCA solid. From the NMR spectrum ( Figure 9 ) analysis, the product of the present embodiment and the IPCA proposed by column chromatography have the same nuclear magnetic signal peak, and there are few miscellaneous peaks, which proves that the sample purity is higher, and the productive rate...

Embodiment 3

[0050] As in Example 1, the fluorescent aqueous solution can also be obtained by changing the feed ratio / hydrothermal temperature / hydrothermal time during synthesis. When other conditions remain unchanged, such as changing the feeding ratio (the molar ratio of acid / amine is changed between 0.25 and 4:1), the properties of the fluorescent aqueous solution are changed ( Figure 10 ). As the proportion of acid increases, the fluorescence quantum yield of the sample gradually decreases; at the same time, if the proportion of acid is too low, the absorption value of the sample decreases, which means that the reaction yield decreases. In summary, it is considered that the feeding ratio of 1:1 is more appropriate.

[0051] Such as changing the water temperature (between 100 and 200°C, Figure 11 ), the quantum yield of the obtained product decreases gradually with the increase of the reaction temperature. At the same time, we found that when the hydrothermal temperature is 150°C, ...

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Abstract

The invention belongs to the technical field of fluorescent molecular dye preparing and purifying and relates to highlight and high-purity water solubility fluorescent molecules and a preparing method thereof, in particular to highlight and high-purity water solubility fluorescent molecules which are prepared through citric acid, ethylenediamine, related derivatives of ethylenediamine or analogues of ethylenediamine through a hydrothermal method and subjected to column chromatography or extraction purification and the preparing method. Compared with marketed fluorochrome, the highlight and high-purity water solubility fluorescent molecules are low in price and have bright and stable blue fluorescence, good fluorescent stability, low biotoxicity and the like, laboratory preparation IPCA synthesis is easy and convenient, and modifying and coupling are facilitated due to the fact that active groups (carboxyl) are contained. The highlight and high-purity water solubility fluorescent molecules have potential application in the field of bioimaging, fluorescence labeling, fluorescence printing and the like.

Description

technical field [0001] The invention belongs to the technical field of preparation and purification of fluorescent molecular dyes, and specifically relates to a class of bright, high-purity water prepared by hydrothermal method of citric acid, ethylenediamine and related derivatives or analogs, and then purified by column chromatography or extraction Soluble fluorescent molecule and its preparation method. Background technique [0002] Water-soluble fluorescent molecules can be used as fluorescent probes for biological tissues, and have very important applications in the field of life sciences. Many types of fluorescent molecules with excellent optical properties have poor water solubility, such as coumarin, rhodamine, and fluorescein. Although appropriate modification can increase their solubility in water, it also increases the difficulty and cost of synthesis. Moreover, their structures are complex and often have high biological toxicity. Alexa fluor dyes are a series ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C09K11/06C09B57/00
CPCC07D471/04C09B57/00C09K11/06C09K2211/1044
Inventor 杨柏宋玉彬付昱朱守俊赵晓欢
Owner JILIN UNIV
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