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1,3,5,7-tetramethyl-8-triphenylamine base pyrrole methane-boron difluoride complex compound and preparation method thereof

A technology of triphenylaminopyrromethene and boron difluoride, which is applied in the field of organic synthesis, can solve the problems of unfavorable detection or observation, increased self-absorption of fluorescent dyes, unfavorable application of live imaging, etc., to achieve wide application and reduce self-absorption Effect

Inactive Publication Date: 2012-01-18
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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Problems solved by technology

However, BODIPY dyes also have their shortcomings. For example, the emission wavelength of BODIPY dyes is usually less than 650nm, which is not conducive to the application in in vivo imaging, and the Stokes shift of BODIPY dyes is usually less than 30nm, which is not conducive to detection or observation. Increased self-absorption of fluorescent dyes
Additionally, BODIPY dyes have not been used as photocatalysts in the prior art

Method used

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  • 1,3,5,7-tetramethyl-8-triphenylamine base pyrrole methane-boron difluoride complex compound and preparation method thereof
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  • 1,3,5,7-tetramethyl-8-triphenylamine base pyrrole methane-boron difluoride complex compound and preparation method thereof

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[0041] The preparation method of the present invention will be specifically described below.

[0042] The first step: 546 mg (2.0 mmol) of 4-formyl triphenylamine and 419 mg (4.4 mmol) of 2,4-dimethylpyrrole were dissolved in 100 mL of dried dichloromethane, and then 20 μL of trifluoroacetic acid was added as a catalyst, A reaction system is formed, and the room temperature is protected from light and stirred overnight to generate the first intermediate;

[0043] The second step: take 454mg (2.0mmol) of oxidant 2,3-dichloro-5,6-dicyano-1,4-p-benzoquinone according to the equimolar ratio with 4-formyltriphenylamine and dissolve it in 10mL In methyl chloride, add it to the reaction system that the first intermediate is generated, and stir at room temperature for 30 min to generate the second intermediate;

[0044] The third step: add 3 mL of triethylamine to the reaction system with the second intermediate, stir at room temperature for 10 min, slowly add 3 mL of boron trifluori...

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Abstract

The invention relates to a 1,3,5,7-tetramethyl-8-triphenylamine base pyrrole methane-boron difluoride complex compound and a preparation method thereof, which belong to the technical field of organic synthesis. The existing photocatalysts have few varieties and low conversion rate, and the existing bodipy dye has low infrared fluorescent efficiency and small Stokes displacement. The invention provides the 1,3,5,7-tetramethyl-8-triphenylamine base pyrrole methane-boron difluoride complex compound. The preparation method comprises the steps that: 4-formoxyl tetramethyl and 2,4-dimethyl pyrrole are dissolved in organic solvents, trifluoroacetic acid or monoprop is used as catalysts, and a reaction system is formed; 2,3-dichloro-5,6-dicyan-1,4-para-benzoquinone with the same mol ratio as the 4-formoxyl tetramethyl is taken, is dissolved in the methylene dichloride and is added into the reaction system; and one of triethylamine, triisopropyl amine and N,N-diisopropylethylamine is added into the reaction system, boron trifluoride etherate is added under the ice bath, and final products are generated.

Description

technical field [0001] The present invention relates to a 1,3,5,7-tetramethyl-8-triphenylamino pyrrolemethine-boron difluoride complex and a preparation method thereof. The substance is a pyrromethine-boron difluoride complex. The derivative belongs to the technical field of organic synthesis. Background technique [0002] Photocatalyst is a general term for a class of chemical substances that have catalytic effects under the excitation of photons, also known as "photocatalysts". The earliest photocatalytic reaction was completed by Fujishima A et al. in 1972, using TiO 2 Single-crystal electrodes act as photocatalysts to achieve photo-splitting of water. Except for TiO 2 In addition, fluorescent dyes such as fluorescein, Nile red, eosin, and ruthenium terpyridine have also been used as photocatalysts, see M.Neumann, S.Füldner, B. K. Zeitler, Angew. Chem. Int. Ed. 50 (2011) 951-954. In addition to photocatalytic water splitting to produce hydrogen, photocatalysts have ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02B01J31/22C07C251/24C07C249/02C07C49/78C07C45/00C09K11/06C09B57/00
Inventor 景遐斌李文亮谢志刚
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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