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Strong fluorescence fluoro-boron dipyrrole compound containing triphenylamine structure as well as preparation method and application thereof

A fluorescent fluoroboron dipyrrole and triphenylamine technology, which is applied in the fields of compounds containing elements of Group 3/13 of the periodic table, chemical instruments and methods, organic chemistry, etc. Fluorescence quantum efficiency, effect of simple synthesis method

Inactive Publication Date: 2013-06-26
CHANGCHUN INST OF OPTICS FINE MECHANICS & PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the prior art, there is no research on the application of fluoroboron dipyrrole compounds as laser dyes

Method used

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  • Strong fluorescence fluoro-boron dipyrrole compound containing triphenylamine structure as well as preparation method and application thereof
  • Strong fluorescence fluoro-boron dipyrrole compound containing triphenylamine structure as well as preparation method and application thereof
  • Strong fluorescence fluoro-boron dipyrrole compound containing triphenylamine structure as well as preparation method and application thereof

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preparation example Construction

[0040] The preparation method of the strong fluorescence boron dipyrrole compound containing triphenylamine structure comprises the following steps:

[0041] (1) Under the protection of an inert atmosphere, weigh formyl-substituted triphenylamine and 2,4-dimethylpyrrole and dissolve them in a dry solvent, add a catalyst, stir and react at room temperature for 6-10 hours in the dark, and obtain a purple-red solution ;

[0042] The formyl-substituted triphenylamine is bis(4-formylphenyl)aniline or tris-(4-formylphenyl)amine;

[0043] (2) Weigh the oxidant and dissolve it in a dry solvent, add it to the purple-red solution obtained in step (1), stir and react at room temperature for 20 to 40 minutes to obtain a black solution;

[0044] (3) Add triethylamine to the black solution, stir at room temperature for 5 to 10 minutes, add boron trifluoride complex, stir and react in an ice bath for 3 to 8 hours, and obtain a reaction solution, which is separated by extraction and reduced ...

Embodiment 1

[0074] Preparation of strong fluorescent fluoroboron dipyrrole compound containing triphenylamine structure of formula (I):

[0075] (1) Weigh 0.274 grams of 4-dianilinobenzaldehyde, and dissolve 0.19 grams of 2,4-dimethylpyrrole in 20 milliliters of anhydrous dichloromethane, add 2 drops (10ul) of trifluoroacetic acid, under nitrogen protection, Magnetically stirred at room temperature for 6 hours to obtain a purple solution;

[0076] (2) 0.3 g of chloranil was dissolved in 10 ml of dichloromethane, added to the above-mentioned purple-red solution, and stirred at room temperature for 30 minutes to obtain a black solution;

[0077] (3) Add 3 milliliters of triethylamine and 3 milliliters of boron trifluoride ether solution to the above black solution, stir at room temperature for 6 hours, add 100 milliliters of water to quench the reaction, extract with dichloromethane, dry the organic phase with anhydrous magnesium sulfate, Concentrated under reduced pressure, the crude prod...

Embodiment 2

[0081] Preparation of strong fluorescent fluoroboron dipyrrole compound containing triphenylamine structure of formula (П) structure:

[0082] (1) Weigh 0.301 g of bis(4-formylphenyl) aniline, dissolve 0.38 g of 2,4-dimethylpyrrole in 40 ml of anhydrous dichloromethane, add 2 drops (10ul) of trifluoroacetic acid as a catalyst , under nitrogen protection, magnetically stirred at room temperature for 8 hours to obtain a purple-red solution;

[0083] (2) 0.455 g of chloranil was dissolved in 20 ml of dichloromethane, added to the above purple-red solution, and stirred at room temperature for 30 minutes to obtain a black solution;

[0084] (3) Add 5 milliliters of triethylamine and 5 milliliters of boron trifluoride ether solution to the above-mentioned black solution, stir at room temperature for 8 hours, add 200 milliliters of water to quench the reaction, extract with dichloromethane, dry the organic phase over anhydrous magnesium sulfate, subtract Concentrate under reduced pr...

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Abstract

The invention relates to a strong fluorescence fluoro-boron dipyrrole compound containing a triphenylamine structure as well as a preparation method and an application thereof, belonging to the technical fields of organic chemical industry and fine chemical industry. The preparation method comprises the following steps of: weighing and dissolving formyl substituted triphenylamine and 2,4-dimethyl pyrrolo in a dry dissolvent under the protection of inert atmosphere; adding a catalyst; reacting at a room temperature in a dark place for 6-10 hours; then adding an oxidant; reacting at room temperature for 20-40 minutes; and finally adding organic amine and a boron triflouride complex compound and reacting for 3-8 hours, thus obtaining the strong fluorescence fluoro-boron dipyrrole compound containing a triphenylamine structure. The synthetic method is simple and convenient, and the synthetic compound serves as a laser dye and has relatively high solution pumping laser efficiency, narrowed ultraviolet and visible absorption spectrum and fluorescence emission spectrum, high fluorescence quantum efficiency and good light stability.

Description

technical field [0001] The invention relates to a strong fluorescent fluoroboron dipyrrole compound containing a triphenylamine structure and a preparation method and application thereof, belonging to the technical fields of organic chemical industry and fine chemical industry. Background technique [0002] In the prior art, lasers are mainly divided into two types, one is lasers that can only produce specific wavelengths, such as: helium-cadmium lasers have a laser wavelength of 325 nanometers, argon lasers have a laser wavelength of 488.5 nanometers, and yttrium-aluminum-garnet lasers (YAG) laser wavelength is 1060 nanometers, and the application of these lasers is subject to many restrictions due to the fixed wavelength of the laser; another kind of laser can continuously output the laser of the required wavelength within a certain range, such as, in 1967, Sorokin used Rhodamine6G dyes to make Dye lasers, which have been extensively studied due to their superior performan...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09B57/00C09K11/06
Inventor 李斌杨杨张黎明刘星元
Owner CHANGCHUN INST OF OPTICS FINE MECHANICS & PHYSICS CHINESE ACAD OF SCI
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