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Pyrrole dimethine fluorescent dyes as well as synthetic method and use thereof

A technology for pyrrole dimethacrylate and fluorescent dyes, which is applied in the field of synthesis of the fluorescent dyes and achieves the effects of good chemical stability and photostability, and suitable excitation and emission wavelengths.

Inactive Publication Date: 2008-06-25
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is precisely because of these unique photochemical and photophysical properties that BODIPY fluorescent dyes have become a research hotspot in the past ten years. At present, people have been able to achieve UV-visible and infrared near-infrared by changing the conjugated chain and substituents. The light region changes its absorption and emission wavelengths arbitrarily, and various dyes are synthesized, but it is still a difficult point to introduce active functional groups on the parent dyes and then use them in the fields of biomarkers and bioanalytical detection.

Method used

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  • Pyrrole dimethine fluorescent dyes as well as synthetic method and use thereof
  • Pyrrole dimethine fluorescent dyes as well as synthetic method and use thereof
  • Pyrrole dimethine fluorescent dyes as well as synthetic method and use thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0028] a. Dissolve styrene and liquid bromine in carbon tetrachloride respectively, and slowly add the carbon tetrachloride solution with liquid bromine into the carbon tetrachloride solution with styrene at 15°C, and stir for 5 After reaction finishes, carbon tetrachloride is distilled off under reduced pressure, obtains white crystal 1,2-dibromostyrene, and described white crystal 1,2-dibromostyrene is dissolved in dimethyl sulfoxide, Slowly add sodium azide under nitrogen protection, stir at 20°C for 24 hours, then add aqueous sodium hydroxide solution to make it in a strong alkaline environment, continue stirring for 36 hours, and then add the reaction product to the sodium bicarbonate solution, and use Dichloromethane extraction, the organic layer was washed with water, and the organic solvent was distilled off under reduced pressure to obtain a dark red oil, which was separated on a silica gel column and eluted with petroleum ether as an eluent, and then evaporated under ...

Embodiment 2

[0033] a. Dissolve styrene and liquid bromine in carbon tetrachloride respectively, and slowly add the carbon tetrachloride solution with liquid bromine into the carbon tetrachloride solution with styrene at 20°C, and stir for 1 After reaction finishes, carbon tetrachloride is distilled off under reduced pressure, obtains white crystal 1,2-dibromostyrene, and described white crystal 1,2-dibromostyrene is dissolved in dimethyl sulfoxide, Slowly add sodium azide under the protection of argon, stir at 28°C for 10 hours, then add aqueous sodium hydroxide solution to make it in a strong alkaline environment, continue stirring for 12 hours, then add the reaction product to sodium bicarbonate solution, and use Dichloromethane extraction, the organic layer was washed with water, and the organic solvent was distilled off under reduced pressure to obtain a dark red oil, which was separated on a silica gel column and eluted with petroleum ether as an eluent, and then evaporated under redu...

Embodiment 3

[0038] Take 5.2 grams (0.05mol) of styrene and dissolve it in carbon tetrachloride, and dissolve 8.0 grams (0.10mol) of liquid bromine in carbon tetrachloride. Keep the temperature in an ice-water bath at 15° C. The carbon solution was slowly added to the carbon tetrachloride solution dissolved in styrene, controlled at 15°C, and stirred for 5 hours. After completion of the reaction, carbon tetrachloride was removed by distillation under reduced pressure to obtain white crystal 1,2-dibromostyrene, and the white crystal 1,2-dibromostyrene was dissolved in dimethyl sulfoxide. Slowly add 4.9 grams (0.075mol) of sodium azide under air protection, keep the temperature at 28°C and continue to stir for 10 hours, then add a certain volume of aqueous solution containing 2.0 grams of sodium hydroxide to the mixture to make it in a strongly alkaline environment, continue After stirring for 12 hours, the reaction product was poured into a certain volume of 2% sodium bicarbonate solution, ...

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Abstract

The invention provides a pyrrole di-methine fluorescent dye and a synthesis method and application; the synthesis method is as follows: a. preparing 2-phenylaziridine from styrene; b. adding 2-phenylaziridine into acetophenone, and reacting to produce 2, 4-diphenylpyrrole in the presence of sodium hydride under room temperature; c. adding 2, 4-diphenylpyrrole into p-hydroxybenzaldehyde, then adding chloranil according to the weight proportion 2, 4-diphenylpyrrole : chloranil =1:3-7; reacting under room temperature with stirring, removing excessive chloranil after reaction, and spinning dry to get blue solid pyrromethene; d. adding blue solid pyrromethene into dichloromethane for dissolution, then adding boron trifluoride diethyl etherate under the protection of inert gas, and reacting under room temperature; after reaction, adding chloroform and extracting 2 to 3 times; combining extract liquids, water washing, drying by anhydrous magnesium sulfate, spinning dry, and column separation to yield products.

Description

Technical field: [0001] The invention relates to a class of novel BODIPY fluorescent dyes with active groups, and also relates to a synthesis method and application of the fluorescent dyes. Background technique: [0002] Fluorescent dyes are modified with specific active groups, which can be used as fluorescent probes to react specifically with specific ions, free radicals, and other substances. Such dyes have great application value in analytical chemistry, life science, environmental science and other fields. At the same time, fluorescent dyes, as laser dyes, have been widely used in many scientific research and production fields, such as spectroscopy, physics, medicine, biophysics, optical fiber technology, photochemistry, astronomy, military industry, etc. Therefore, the synthesis of new fluorescent dyes is of great significance in the fields of scientific research and production. [0003] BODIPY-type fluorescent dyes are a relatively new fluorescent compound that has ...

Claims

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Application Information

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IPC IPC(8): C09B23/16C09B62/00C09K11/06G01N33/533
Inventor 唐波李普明李平段霞于法标
Owner SHANDONG NORMAL UNIV
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