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Pyrromethene-boron difluoride complex derivative and preparation method thereof

A technology of boron difluoride and pyrromethine, which is applied in the field of pyrromethine-boron difluoride complex derivatives and its preparation, can solve the problems of low laser efficiency, difficult boron difluoride complex modification compounds, Narrow laser tuning range and other issues, to achieve the effect of simple synthesis method, rich structure and functional diversity

Inactive Publication Date: 2015-08-26
NORTHEAST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The 1,3,5,7-tetramethyl-2,6-dimethyl-8-(4-methoxyphenyl)pyrromethene-boron difluoride complex with application number 01126813.1 solves the problem of fluorescent dyes High triplet absorption, narrow laser tuning range and low laser efficiency and other defects, but the chemical properties of the introduced methoxyphenyl group are relatively stable. When used as a fluorescent dye, it is difficult to combine pyrromethene-two Boron fluoride complex modification to the compound to be detected

Method used

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  • Pyrromethene-boron difluoride complex derivative and preparation method thereof
  • Pyrromethene-boron difluoride complex derivative and preparation method thereof
  • Pyrromethene-boron difluoride complex derivative and preparation method thereof

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example

[0038]1,3,5,7-Tetramethyl-8-(4-allyloxyphenyl)pyrromethene-boron difluoride complex was used as a probe for detecting proteins, and the experiment was as follows: In No. 1 and Add concentration is the Tris-Hcl buffer solution of 0.5mol / L and the NaCl solution of 0.4mol / L in No. 2 absorption pool, adjust pH value to 7.4, then add the 1 that concentration is 0.03mmol / L in No. 1 absorption pool, 3,5,7-Tetramethyl-8-(4-allyloxyphenyl)pyrromethene-boron difluoride complex solution 2mL, scan its absorption spectrum in the wavelength range of 300-800nm, the excitation wavelength Fix around the wavelength of the maximum absorption peak, add 2mL of r-globulin solution with a concentration of 0.03mmol / L to No. 1 and No. 2 absorption pools respectively, and measure the fluorescence intensity F of No. 1 absorption pool 1 , the fluorescence intensity of No. 2 absorption cell is F 2 ; while the fluorescence intensity of 1,3,5,7-tetramethyl-8-(4-allyloxyphenyl)pyrromethene-boron difluoride ...

example 1

[0042] Step 1: Under the condition of protecting from light and nitrogen at room temperature, add 100 mL of anhydrous dichloromethane to a reactor equipped with a stirrer, then add 419 mg (4.4 mmol) of 2,4-dimethylpyrrole and 4-ene After propoxybenzaldehyde 546mg (2.0mmol), the stirrer was turned on, and then 20 μL of catalyst was added to react with trifluoroacetic acid for 10 hours;

[0043] Step 2: Dissolve 454mg of the oxidizing agent 2,3-dichloro-5,6-dicyano-1,4-p-benzoquinone in 10mL of dichloromethane, then add it into the reaction kettle, and stir at room temperature for 30min;

[0044] Step 3: Add 3 mL of triethylamine, stir at room temperature for 10 min, slowly add 5 mL of boron trifluoride ether in an ice bath, and continue stirring for 3 h;

[0045] Step 4: sequentially wash with water, dry, evaporate the solvent under reduced pressure, use n-hexane:ethyl acetate=10:1 (volume ratio) as the eluent, and conduct column chromatography separation with silica gel as the...

example 2

[0049] Step 1: Under the condition of protecting from light and nitrogen at room temperature, add 100 mL of anhydrous dichloromethane to a reaction kettle equipped with a stirrer, then add 419 mg (4.4 mmol) of 2,4-dimethylpyrrole and 4-ene After propoxybenzaldehyde 546mg (2.0mmol), the stirrer was turned on, and then 20 μL of catalyst was added to react with trifluoroacetic acid for 10 hours;

[0050] Step 2: Dissolve 454mg of the oxidizing agent 2,3-dichloro-5,6-dicyano-1,4-p-benzoquinone in 10mL of dichloromethane, then add it into the reaction kettle, and stir at room temperature for 30min;

[0051] Step 3: Add 3 mL of triisopropylamine, stir at room temperature for 10 min, slowly add 5 mL of boron trifluoride diethyl ether in an ice bath, and continue stirring for 8 h;

[0052] Step 4: sequentially wash with water, dry, evaporate the solvent under reduced pressure, use n-hexane:ethyl acetate=10:1 (volume ratio) as the eluent, and conduct column chromatography separation wi...

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Abstract

The invention provides a pyrromethene-boron difluoride complex derivative. A 1,3,5,7-tetramethyl-8-(4-allyloxy phenyl) pyrromethene-boron difluoride complex is formed by substituting allyloxy phenyl for a group on C8 of the pyrromethene-boron difluoride complex, the derivative contains specific 4-allyloxy phenyl group, so that the compound reactivity is improved greatly, and introduction of the 1,3,5,7-tetramethyl-8-(4-allyloxy phenyl) pyrromethene-boron difluoride complex as a group to a to-be-detected matter molecule is facilitated. The invention further provides a preparation method of the pyrromethene-boron difluoride complex derivative. The synthetic method is simple, intermediate separation is not required, and multiple steps of reactions are finished in one pot.

Description

technical field [0001] The invention relates to the technical field of organic synthesis. More specifically, the present invention relates to a derivative of pyrromethene-boron difluoride complex and a preparation method thereof. Background technique [0002] The core structure of the pyrromethene-boron difluoride complex is shown below: [0003] [0004] The two pyrrole rings are connected by a formazan bridge and a boron atom to form a rigid conjugated planar structure as shown in the above formula. The dye has obvious fluorescence characteristics, and its fluorescence quantum yield is high, and it can exist stably under physiological conditions. . Modification of its structure can improve its fluorescence properties very well. As fluorescent dyes, pyrromethine-boron difluoride complexes are widely used as biosensors, ion probes, photodynamic therapy, biomarkers and photosensitizers. Agents, etc., have proved the diversity and wide application value of the pyrromethe...

Claims

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Application Information

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IPC IPC(8): C07F5/02
CPCC07F5/022
Inventor 李文亮姜默李玉新
Owner NORTHEAST NORMAL UNIVERSITY
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