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Fluorescent boron dipyrrole fluorescent dye and its preparation method and application

A technology of fluorobodipyrrole and fluorescent dyes, which is applied in the field of fluorescent dyes, can solve the problems of small red shift and limited application, and achieve the effect of improving electron-withdrawing ability and high quantum yield

Active Publication Date: 2022-04-26
NANJING TECH UNIV +1
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Problems solved by technology

However, the red shift of the existing fluoroboron dipyrrole fluorescent dyes is relatively small
For example, in the prior art "Photophysical Properties of Borondipyrromethene Analogues in Solution" (J.Phy.Chem.A 2005, 109, 7371-7384), a benzene ring is introduced at the 8th position of the BODIPY core, and a methyl group is introduced at the 3rd and 5th positions, The obtained fluoroboron dipyrrole derivative has a stronger absorption peak at 520nm and a stronger emission peak at 525nm, making it suitable for use in green photosensitizers, green fluorescent probes, and light-emitting layers of organic light-emitting diodes restricted

Method used

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  • Fluorescent boron dipyrrole fluorescent dye and its preparation method and application
  • Fluorescent boron dipyrrole fluorescent dye and its preparation method and application
  • Fluorescent boron dipyrrole fluorescent dye and its preparation method and application

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preparation example Construction

[0027] The present invention also provides a method for preparing the fluorobodipyrrole fluorescent dye described in the above technical solution, comprising the following steps:

[0028] mixing pyrrole, p-tolualdehyde and trifluoroacetic acid, and carrying out condensation reaction under a protective atmosphere to obtain the intermediate shown in formula II;

[0029] Under a protective atmosphere, mix the tetrahydrofuran solution of the intermediate represented by formula II and N-bromosuccinimide at -80 to -76°C, and after the N-bromosuccinimide is dissolved, add 2 , 3-dichloro-5,6-dicyano-1,4-benzoquinone in tetrahydrofuran solution, and then carry out bromination reaction at room temperature to obtain the intermediate shown in formula III;

[0030] Mixing the intermediate represented by the formula III with triethylamine, boron trifluoride ethyl ether, and dichloromethane, and performing a fluoroboration reaction to obtain the intermediate represented by the formula IV;

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Embodiment 1

[0061] (1) Preparation of intermediates shown in formula Ⅱ

[0062] Pyrrole (27.8mL, 400mmol) was mixed with p-tolualdehyde (2.36mL, 20mmol), stirred and reacted under nitrogen atmosphere for 15min, then added trifluoroacetic acid (0.15mL, 2mmol), stirred and reacted for 14h, and then the resulting reaction solution was mixed with Mix 50mL of 0.1M sodium hydroxide solution and 100mL of dichloromethane for the first extraction, wash the obtained organic phase twice with 50mL of water each time, then wash with saturated saline and anhydrous magnesium sulfate in sequence Dry, then carry out vacuum distillation to remove unreacted pyrrole, and carry out the first column chromatography of the obtained residue, the eluent used is petroleum ether, ethyl acetate and triethylamine according to the volume ratio of 8:2:1 mixed The obtained mixed solution was vacuum-dried the obtained fraction containing the target product to obtain the intermediate represented by formula II as a reddish-...

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Abstract

The invention provides a fluoroborate dipyrrole fluorescent dye, a preparation method and application thereof, and belongs to the field of fluorescent dyes. The invention provides a fluoroboron dipyrrole fluorescent dye, centering on BODIPY, introducing toluene at the 8th position, increasing the conjugated system, introducing propylene at the 3rd and 5th positions, improving the electron-absorbing ability, making The ultraviolet absorption spectrum and the fluorescence emission spectrum of the obtained fluoroboron dipyrrole fluorescent dye have a large red shift, a strong absorption peak in the green light range, and a strong emission peak in the green light range in the fluorescence emission spectrum.

Description

technical field [0001] The invention relates to the field of fluorescent dyes, in particular to a fluoroboron dipyrrole fluorescent dye and a preparation method and application thereof. Background technique [0002] Fluorescent dyes have been around for nearly a century and have attracted the attention of scientists from multiple disciplines. Fluorescent dyes are used as functional materials in many fields, such as light energy conversion, organic light-emitting devices, biological imaging, diagnosis and treatment, etc., and have made great progress. Many kinds of highly fluorescent organic dyes have been found now. As one of many dyes, fluoroboron dipyrrole fluorescent dyes have high fluorescence quantum yield and molar extinction coefficient, and also have strong photostability and Chemical stability has attracted the attention of many researchers. However, the red shift of the existing fluoroborate dipyrrole fluorescent dyes is relatively small. For example, in the pri...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B57/00C07F5/02C09K11/06H01L51/54G01N21/64
CPCC09B57/00C07F5/022C09K11/06G01N21/6428C09K2211/1055C09K2211/1007H10K85/657
Inventor 刘睿程乾潘苑潘汝滨晋圣中朱红军
Owner NANJING TECH UNIV
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