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Asymmetric near-infrared BODIPY fluorescent dye as well as preparation method and application thereof

A fluorescent dye and near-infrared technology, which is used in the preparation and application of fluorescent dyes, can solve the problems of poor water solubility, limited application, and lack of groups, and achieve the effects of saving raw materials, simple and easy preparation methods, and good photostability

Inactive Publication Date: 2015-05-27
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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  • Asymmetric near-infrared BODIPY fluorescent dye as well as preparation method and application thereof
  • Asymmetric near-infrared BODIPY fluorescent dye as well as preparation method and application thereof
  • Asymmetric near-infrared BODIPY fluorescent dye as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] A kind of asymmetric near-infrared BODIPY fluorescent dye, chemical formula is C 18+m h 13+n BF 2 N 2+x o y , where m is 3, n is 4, x is 1, y is 3, and the molecule has the following structure:

[0034] ,

[0035] where: R 1 , R 2 , R3 for H, R 4 is acetoxy, R 5 , R 6 is a fluorine atom,

[0036] Its preparation method steps are as follows:

[0037] 1) Dissolve 0.34 ml (2.4 mmol) of pyrrole in 50 ml of toluene, add 220 mg (1 mmol) of 8-acetoxyquinoline-2-carbaldehyde under nitrogen atmosphere to obtain a mixed solution, 2) under nitrogen protection , adding 5 microliters of catalyst trifluoroacetic acid dropwise to the reaction solution, and reacting at a temperature of 0° C. for 3 hours to obtain a reaction solution;

[0038] 3) Add 245 mg of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to the above reaction solution, the mixture of DDQ and 8-acetoxyquinoline-2-carbaldehyde The molar ratio is 1.1:2, and the oxidative dehydrogenation is carried out for...

Embodiment 2

[0046] Embodiment 2: A kind of asymmetrical near-infrared BODIPY fluorescent dye, chemical formula is C 18+m h 13+n BF 2 N 2+x o y , where m is 3, n is 4, x is 1, y is 3, and the molecule has the following structure:

[0047] ,

[0048] where: R 1 , R 2 , R 3 for H, R 4 is acetoxy, R 5 , R 6 is a fluorine atom,

[0049] Its preparation method steps are as follows:

[0050] 1) 7.0 ml of pyrrole was dissolved in 10 ml of dichloromethane, and 0.10 ml of 8-acetoxyquinoline-2-carbaldehyde was added under a nitrogen atmosphere to obtain a mixed solution;

[0051] 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;

[0052] 3) Add 2.24 grams of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to the above reaction solution, the mixture of DDQ and 8-acetoxyquinoline-2-carbaldehyde The molar ratio is 10.0:1, and the oxid...

Embodiment 3

[0059] A kind of asymmetric near-infrared BODIPY fluorescent dye, chemical formula is C 18+m h 13+n BF 2 N 2+x o y , where m is 3, n is 4, x is 1, y is 3, and the molecule has the following structure:

[0060] ,

[0061] where: R 1 , R 2 , R 3 for H, R 4 is acetoxy, R 5 , R 6 is a fluorine atom,

[0062] Its preparation method steps are as follows:

[0063] 1) Dissolve 0.2 ml of pyrrole in 50 ml of ether, and add 0.10 ml of 8-acetoxyquinoline-2-carbaldehyde under nitrogen atmosphere to obtain a mixed solution;

[0064] 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;

[0065]3) Add 2.3 mg of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to the above reaction solution, the mixture of DDQ and 8-acetoxyquinoline-2-carbaldehyde The molar ratio is 0.01:1, and the oxidative dehydrogenation is carried out for 0.5 ho...

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PUM

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Abstract

The invention discloses an asymmetric near-infrared BODIPY fluorescent dye. The chemical formula of the dye is C(18+m)H(13+n)BF2N(2+x)Oy, wherein m, n, x and y are all integer within 1 to 100. The preparation method of the dye comprises the following steps: dissolving a substituent group-containing pyrrole solution in an organic solvent; adding a quinolinaldehyde derivative at presence of nitrogen to perform catalytic reaction; adding 2,3-dichloro-5,6-dicyano-1,4-benzoquinone for oxidative dehydrogenation; finally adding organic amine and a boron trifluoride diethyl ether solution; reacting again; concentrating a reaction solution; performing chromatography by utilizing a silica gel column to obtain the asymmetric near-infrared BODIPY fluorescent dye. The asymmetric near-infrared BODIPY fluorescent dye disclosed by the invention has the advantages of being narrow in ultraviolet visible absorption spectrum and fluorescence emission spectrum and good in optical stability, can be applied to cell imaging, fluorescence probes or laser dyes, and is good in practical application; the method is simple and easy to implement, can be used for obtaining near-infrared BODIPY without multi-step reaction, can save raw materials and is easy to popularize and apply practically.

Description

technical field [0001] The invention relates to the preparation and application of fluorescent dyes, in particular to an asymmetric near-infrared BODIPY fluorescent dye and its preparation 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 biomarking. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/00C09K11/06G01N21/64
Inventor 曾林涛查佳玉徐俊超何媛媛郝然
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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