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Novel BODIPY flourescent dye with adjustable emission wavelength and preparation method thereof

A fluorescent dye and emission wavelength technology, applied in the field of bioluminescent analysis, can solve the problems of poor water solubility, lack of groups, and limited applications, etc., and achieve the effect of simple molecular structure, simple synthesis method, and good photostability

Inactive Publication Date: 2013-07-10
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 BODIPY flourescent dye with adjustable emission wavelength and preparation method thereof
  • Novel BODIPY flourescent dye with adjustable emission wavelength and preparation method thereof
  • Novel BODIPY flourescent dye with adjustable emission wavelength and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] A BODIPY fluorescent dye with adjustable emission wavelength, chemical formula is C 19 h 14 BF 7 N 2 , the preparation method steps are as follows:

[0033] 1) Dissolve 196 mg of pentafluorobenzaldehyde in 10 ml of anhydrous dichloromethane, add 9.6 ml of 2,4-dimethylpyrrole under a nitrogen atmosphere to obtain a mixed solution, pentafluorobenzaldehyde and 2,4-di The molar ratio of methylpyrrole is 1:100;

[0034] 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;

[0035]3) Add 2.57 grams of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to the above reaction solution, the molar ratio of DDQ to pentafluorobenzaldehyde is 10:1, Oxidative dehydrogenation for 0.5 hours to obtain a dehydrogenation solution;

[0036] 4) Add 1.4 ml of triethylamine and 1.9 ml of boron trifluoride ether solution in sequence to the above d...

Embodiment 2

[0042] A BODIPY fluorescent dye with adjustable emission wavelength, chemical formula is C 19 h 14 BF 7 N 2 , the preparation method steps are as follows:

[0043] 1) Dissolve 196 mg of pentafluorobenzaldehyde in 10 ml of anhydrous chloroform, add 9.7 ml of 2,4-dimethylpyrrole under a nitrogen atmosphere to obtain a mixed solution, pentafluorobenzaldehyde and 2,4-dimethyl The molar ratio of pyrrole is 1:100;

[0044] 2) Under the protection of nitrogen, add 5 mg of catalyst p-toluenesulfonic acid to the reaction solution, and react at 0°C for 3 hours to obtain the reaction solution;

[0045] 3) Add 257 mg of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to the above reaction solution, the molar ratio of DDQ to pentafluorobenzaldehyde is 1:1, Oxidative dehydrogenation for 0.5 hours to obtain a dehydrogenation solution;

[0046] 4) Add 1.4 ml of triethylamine and 1.9 ml of boron trifluoride ether solution in sequence to the above dehydrogenation solution, the molar ratio...

Embodiment 3

[0051] A BODIPY fluorescent dye with adjustable emission wavelength, chemical formula is C 19 h 14 BF 7 N 2 , the preparation method steps are as follows:

[0052] 1) Dissolve 1.96 g of pentafluorobenzaldehyde in 100 ml of anhydrous dichloromethane, add 0.97 ml of 2-ethylpyrrole under a nitrogen atmosphere to obtain a mixed solution, the molar ratio of pentafluorobenzaldehyde to 2-ethylpyrrole It is 1:2.

[0053] 2) Under nitrogen protection, 5 microliters of catalyst trifluoroacetic acid was added dropwise to the reaction solution, and reacted at a temperature of 25°C for 3 hours to obtain a reaction solution;

[0054] 3) Add 257 mg of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to the above reaction solution, the molar ratio of DDQ to pentafluorobenzaldehyde is 0.1:1, Oxidative dehydrogenation for 0.5 hours to obtain a dehydrogenation solution;

[0055] 4) Add 1.75 ml of diisopropylethylamine and 1.9 ml of boron trifluoride ether solution in sequence to the above d...

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Abstract

The invention relates to a novel BODIPY flourescent dye with an adjustable emission wavelength. The chemical formula of the novel BODIPY flourescent dye is C15+mH6+nBF7N2+xOy, wherein m, n, x and y are integers from 0 to 100. The preparation method comprises the following steps of: dissolving pentafluorobenzaldehyde into an organic solvent, adding pyrrole with substituent groups R1, R2, R3 in the presence of nitrogen, and reacting by taking trifluoroacetic acid or para-toluenesulfonic acid as a catalyst; then adding 2,3-dichloro-5,6-dicyano-1,4-benzoquinone for oxidative dehydrogenation; and finally adding organic amine and boron trifluoride diethyl etherate solutions for continuous reaction, and concentrating a reaction liquid to obtain a target object by utilizing silica gel column chromatography. The novel BODIPY flourescent dye disclosed by the invention can be used for cell imaging and the like, can be adjusted in emission wavelength from a visible region to a near-infrared region and has the advantages of narrow fluorescence emission spectrum, high fluorescence quantum efficiency, good light stability, simple molecular structure, easiness and convenience for synthetic method and easiness for popularization and application.

Description

technical field [0001] The invention relates to a fluorescent dye in the field of biological fluorescence analysis and its preparation, in particular to a BODIPY (boron fluoride complexed dipyrromethene) fluorescent dye with adjustable emission wavelength and a preparation method thereof. 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 emis...

Claims

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Application Information

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IPC IPC(8): C09B23/12G01N33/52
Inventor 曾林涛徐俊超查佳玉王亮王秋生
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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