Taurine substituted bodipy fluorescent compound and preparation method and application thereof

A fluorescent compound, the technology of fluoborofluorescein, which is applied in the field of taurine-substituted fluoborofluorescein fluorescent compounds and its preparation, can solve the problems of low atom economy, unfriendly organometallic reagents, and lengthy steps, etc., and achieve high fluorescence Effects of quantum yield, increased diversity, ease of synthesis

Inactive Publication Date: 2018-08-07
HUBEI GRAND LIFE SCI & TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In order to realize the functional diversity of fluoborofluorene derivatives, scientists must embed different groups on the fluoborofluorene core, but the traditional synthesis method is not only tedious and has low atom economy, but also produces environmentally unfriendly organometallic reagents

Method used

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  • Taurine substituted bodipy fluorescent compound and preparation method and application thereof
  • Taurine substituted bodipy fluorescent compound and preparation method and application thereof
  • Taurine substituted bodipy fluorescent compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] TB-a (2,3,6,-triiodo-8-(4-methylphenyl)-5-taurine substituted flubororine) and TB-b (8-(4-methylphenyl )-3,5-bis-taurine substituted borofluores) Synthesis

[0055]

[0056] (1) Add pyrrole (67.1g, 1mol) and 4-methylbenzaldehyde (6.0g, 50mmol) into a dry light-proof reactor at room temperature under nitrogen protection, and after stirring for 10 minutes in the dark, add 1.0mL three Fluoroacetic acid, after the dropwise addition was completed, the reaction was stopped after stirring for 4 hours. The reaction was quenched with 20 mL of 0.1 M aqueous NaOH and extracted with 100 mL of ethyl acetate. The organic phase was washed twice with water, dried with anhydrous Na2SO4, filtered, the solvent was removed, and 3,4-dimethylpyrrole was recovered under reduced pressure. The residue was washed twice with water, dried with anhydrous Na2SO4, filtered, the solvent was removed, and the pyrrole derivative was recovered under reduced pressure. The residue was subjected to col...

Embodiment 2

[0059] TC-a (3-iodo-8-(4-methoxyphenyl)-5-taurine substituted borofluorene) and TC-b (2,6,-diiodo-8-(4-methyl Synthesis of oxyphenyl)-3,5-bistaurine substituted flubororine)

[0060]

[0061] (1) Pyrrole (67.1g, 1mol) and 4-methoxybenzaldehyde (7.0g, 50mmol) were added to a dry reactor at room temperature under nitrogen protection, and after stirring for 10min in the dark, 1.0mL was added dropwise to the system After the addition of trifluoroacetic acid was completed, the reaction was stopped after stirring for 4 hours. The reaction was quenched with 20 mL of 0.1M aqueous NaOH and extracted with 100 mL of ethyl acetate. After washing the organic phase twice with water, the 2 SO 4 Dry, filter, remove the solvent, and recover 3,4-dimethylpyrrole under reduced pressure. The residue was washed twice with water, and washed with anhydrous Na 2 SO 4 Dry, filter, remove the solvent, and recover the pyrrole derivative under reduced pressure. CH 2 Cl 2 / Petroleum ether / Et 3...

Embodiment 3

[0064] Dissolve B in THF to make 5.0×10 -6 mol / L solution, take 2.5mL and put it into a cuvette, and measure the ultraviolet-visible-near-infrared absorption and fluorescence emission spectra. The maximum absorption peak of the absorption spectrum of B is located at 573nm, and the molar extinction coefficient reaches 2.7×10 5 m -1 cm -1 ( figure 1 ). The maximum absorption peak of the fluorescence emission spectrum is located at 595nm ( figure 2 ), the quantum yield is 0.11.

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Abstract

The invention provides a taurine substituted bodipy fluorescent compound, and further provides a preparation method of the taurine substituted bodipy fluorescent compound. The method comprises the following steps: reacting 8-(4-position substituted phenyl)-3, 5-diiodo-1, 2, 6, 7-tetra-substituted bodipy and 1,2-disubstituted taurine under the conditions of an additive, a catalyst and a solvent toobtain 8-(4-position substituted phenyl) 3-iodo-5-(2-ethanesulfonic acid) amine)-1,2,6,7-tetra-substituted bodipy and 8-(4-position substituted phenyl) 3,5-bis((2-ethanesulfonic acid) amine)-1,2,6,7-tetra-substituted bodipy. According to the taurine substituted bodipy fluorescent compound, by a cheap metal catalyzed direct C-X/N-H activating method, taurine with biological activity is introducedat a 3,5 activated site of star fluorescent molecule bodipy, and therefore, a novel fluorescent molecule framework is formed.

Description

technical field [0001] The application belongs to the technology of organic small molecule functional fluorescent dyes, more specifically, the application relates to a class of taurine-substituted fluoroboron fluorescent compounds and its preparation method and application. Background technique [0002] Taurine (2-aminoethanesulfonic acid), as a sulfur-containing amino acid with a simple structure, exists in a large amount in all organs of humans and animals in free form, and is an important nutrient for humans and animals. And because it is a free amino acid with abundant content in neurons, it has various biological functions such as regulating intracellular calcium homeostasis, scavenging oxygen free radicals and stabilizing cell membranes. Therefore, it is widely welcomed in some functional drinks and health products at home and abroad [see: (a) Huxtable, R.J.; Physiol Rev., 1992, 72, 101; (b) Bakker, A.J.; Berg, H.M.; J. Physiol., 2002, 538, 185-194.]. However, due to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06C09B57/00A61K41/00
CPCA61K41/0057C07F5/027C09B57/00C09K11/06C09K2211/1007C09K2211/1029C09K2211/1055
Inventor 孙华君江汝泳郭晨何本斌
Owner HUBEI GRAND LIFE SCI & TECH CO LTD
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