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Novel red BODIPY fluorescent dye and preparation method and application thereof

A fluorescent dye and red light technology, which is applied in the field of fluorescent dye and its preparation, can solve the problems of limited application, poor water solubility, lack of groups, etc., and achieve the effect of simple synthesis method, simple molecular structure and good photostability

Inactive Publication Date: 2012-10-03
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] At present, most BODIPY dyes have poor water solubility and lack functional groups, which limits their further application in biomedicine.

Method used

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  • Novel red BODIPY fluorescent dye and preparation method and application thereof
  • Novel red BODIPY fluorescent dye and preparation method and application thereof
  • Novel red BODIPY fluorescent dye and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] A preparation method of a novel red light BODIPY fluorescent dye, the steps are as follows:

[0035] 1) Dissolve 0.25 ml of 2-ethylpyrrole in 50 ml of toluene, add 0.10 ml of ethyl glyoxylate under a nitrogen atmosphere to obtain a mixed solution, the organic solvent and the substituent R in the mixed solution 1 , R 2 , R 3 The volume ratio of pyrrole is 200:1, ethyl glyoxylate and substituent R 1 , R 2 , R 3 The molar ratio of pyrrole is 1:2.4;

[0036]2) Under the protection of nitrogen, add 5 microliters of catalyst trifluoroacetic acid dropwise to the reaction solution, and react at a temperature of 0°C for 3 hours to obtain a reaction solution;

[0037] 3) Add 245 mg of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to the above reaction solution, and the molar ratio of DDQ to ethyl glyoxylate is 1.1:1 , oxidative dehydrogenation for 0.5 hour to obtain dehydrogenation liquid;

[0038] 4) Add 0.12 ml of triethylamine and 0.16 ml of boron trifluoride ether so...

Embodiment 2

[0047] A preparation method of a novel red light BODIPY fluorescent dye, the steps are as follows:

[0048] 1) Dissolve 10 ml of 2-ethylpyrrole in 10 ml of dichloromethane, and add 0.10 ml of ethyl glyoxylate under nitrogen atmosphere to obtain a mixed solution, in which organic solvent and substituent R 1 , R 2 , R 3 The volume ratio of pyrrole is 1:1, ethyl glyoxylate and substituent R 1 , R 2 , R 3 The molar ratio of pyrrole is 1:100;

[0049] 2) Under nitrogen protection, 5 microliters of the catalyst p-toluenesulfonic acid was added dropwise to the reaction liquid, and reacted at a temperature of 100°C for 3 hours to obtain a reaction liquid;

[0050] 3) Add 2.24 grams of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to the above reaction solution, and the molar ratio of DDQ to ethyl glyoxylate is 10.0:1 , oxidative dehydrogenation for 0.5 hour to obtain dehydrogenation liquid;

[0051] 4) Add 3 ml of trimethylamine and 4 ml of boron trifluoride ether solution in...

Embodiment 3

[0057] A preparation method of a novel red light BODIPY fluorescent dye, the steps are as follows:

[0058] 1) Dissolve 0.2 ml of 2-ethylpyrrole in 50 ml of ether, add 0.10 ml of ethyl glyoxylate under nitrogen atmosphere to obtain a mixed solution, in which organic solvent and substituent R 1 , R 2 , R 3 The volume ratio of pyrrole is 1:250, ethyl glyoxylate and substituent R 1 , R 2 , R 3 The molar ratio of pyrrole is 1:500;

[0059] 2) Under the protection of nitrogen, add 5 microliters of catalyst trifluoroacetic acid dropwise to the reaction solution, and react at a temperature of 20°C for 3 hours to obtain a reaction solution;

[0060] 3) Add 2.3 mg of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to the above reaction solution, and the molar ratio of DDQ to ethyl glyoxylate is 0.01:1 , oxidative dehydrogenation for 0.5 hour to obtain dehydrogenation liquid;

[0061] 4) Add 30 ml of diisopropylethylamine and 80 ml of boron trifluoride ether solution in sequence ...

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Abstract

The invention relates to a novel red BODIPY fluorescent dye with the chemical formula of C10+mH7+nBF2N2+xOy, wherein m, n, x and y are integers from 0 to 100. The preparation method comprises the following steps: dissolving pyrrole with substituent groups R1, R2 and R3 in an organic solution; adding ethyl glyoxylate together with nitrogen to the organic solution for a chemical reaction by using trifluoroacetic acid or toluenesulfonic acid as a catalyst; adding 2,3-dichloro-5,6-dicyano-1,4-benzoquinone oxidative dehydrogenation; and adding organic amine and a boron trifluoride diethyl ether solution for another reaction. After the reaction solution is concentrated, chromatography is performed with a silicagel column to obtain the fluorescent dye. The fluorescent dye can be used for cell imaging, fluorescent probe or laser dye. The fluorescent dye has the advantages that the ultraviolet-visible absorption spectrum and the fluorescence emission spectrum of the fluorescent dye are narrow; fluorescent quanta has high efficiency and good light stability; and the fluorescent dye has simple molecular structure and can be synthesized easily, so as to facilitate popularization and application.

Description

technical field [0001] The invention relates to a fluorescent dye and its preparation method and application, in particular to a novel red light BODIPY fluorescent dye and its preparation method and application. Background technique [0002] Boron fluoride complex and dipyrromethene fluorescent dye (BODIPY) is a new type of fluorescent dye that has emerged in recent years. It is a complex formed by dipyrromethene and boron trifluoride. The dye molecule has high stability, which can avoid the rapid degradation of the dye structure caused by the irradiation of the excitation light, the rise of temperature or the change of the detection environment of the dye itself during the fluorescence analysis process, and also ensure the stability of the spectral analysis signal . In addition, BODIPY dye has the advantages of high fluorescence quantum efficiency, narrow absorption spectrum and fluorescence emission spectrum, so it has high sensitivity in biological analysis and biomarkin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/04C09K11/06C12Q1/02
Inventor 曾林涛查佳玉王秋生
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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