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Fluorine-containing pyrrole diphenylacerylene organic solid fluorescent compound and synthetic method and application

A technology of pyrrole tolan and fluorescent compounds, which is applied in the fields of organic chemistry, chemical instruments and methods, and luminescent materials, can solve problems such as limiting the application range of organic luminescent materials, and achieve simple and easy synthesis methods, high yields, and long-term The effect of fluorescence lifetime

Inactive Publication Date: 2016-06-22
SOUTH CHINA NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Aggregation-induced quenching greatly limits the application range of organic light-emitting materials

Method used

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  • Fluorine-containing pyrrole diphenylacerylene organic solid fluorescent compound and synthetic method and application
  • Fluorine-containing pyrrole diphenylacerylene organic solid fluorescent compound and synthetic method and application
  • Fluorine-containing pyrrole diphenylacerylene organic solid fluorescent compound and synthetic method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] The synthesis of 3,4-difluoro-1-(4-(2-(4-methoxyphenyl)ethynyl)phenyl)-1H-pyrrole-2-carbaldehyde (ACHO-1) comprises the following steps:

[0055] (1) Synthesis of 2-formyl-3,4-difluoro-1-(4-iodobenzene)-1-H-pyrrole (ICHO-1)

[0056] DMF (70 mL) was added into the three-necked flask, cooled to 0°C, and kept at 0°C, then phosphorus oxychloride (18.5 mL) was slowly dropped into it, after the drop was completed, the temperature was raised to room temperature, and stirred for 4 h. Dissolve 3,4-difluoro-1-(4-iodobenzene)-1H-pyrrole (2g, 6.56mmol) in DMF (15mL), drop into the reaction system drop by drop, after the drop is complete, move the device to 90°C Heat the reaction in an oil bath for 3h. After the reaction is completed, cool to room temperature, pour the reaction system into ice water, neutralize with NaOH solid, add dichloromethane, then wash with water and saturated brine respectively, and wash the organic layer with anhydrous NaOH 2 SO 4 dry. Column chromatogra...

Embodiment 2

[0068] Synthesis of 3-ethoxy-4-fluoro-1-(4-(2-(4-methoxyphenyl)ethynyl)phenyl)-1H-pyrrole-2-carbaldehyde (ACHO-2), including The following steps:

[0069] (1) Synthesis of 2-formyl-3,4-difluoro-1-(4-iodobenzene)-1-H-pyrrole (ICHO-1)

[0070] With embodiment 1 step (1).

[0071] (2) Synthesis of 3-ethoxy-4-fluoro-1-(4-iodophenyl)-1H-pyrrole-2-carbaldehyde (ICHO-2)

[0072] Dissolve 2-formyl-3,4-difluoro-1-(4-iodobenzene)-1H-pyrrole (3.59g, 10mmol) in ethanol (50mL), then add solid sodium hydroxide (8.0g, 200mmol) , stirred overnight at room temperature. After the reaction was completed, the solvent was spun off, diluted with dichloromethane, the organic layer was washed with water and saturated brine respectively, and the separated organic layer was washed with anhydrous Na 2 SO 4 After drying, column chromatography was performed with petroleum ether:ethyl acetate (V:V=5:1) as eluent to obtain a white solid.

[0073]

[0074] The structural characterization data of the...

Embodiment 3

[0084] The synthesis of 3,4-difluoro-1-(4-(2-(4-methoxyphenyl)ethynyl)phenyl)-1H-pyrrole-2-carbonitrile (ACN-1) involved the following step

[0085] (1) Synthesis of 2-formyl-3,4-difluoro-1-(4-iodobenzene)-1-H-pyrrole (ICHO-1)

[0086] With embodiment 1 step (1).

[0087] (2) Synthesis of 2-cyano-3,4-difluoro-1-(4-iodobenzene)-1H-pyrrole (ICN-1)

[0088] The product (1.38g, 4.144mmol) of step (1) was dissolved in methanol (20mL) under reflux, and then slowly dropped into hydroxylamine hydrochloride (0.436g, 6.216mmol) and Na 2 CO 3 (0.66g, 6.216mmol) in aqueous solution (10mL), the reaction system was heated to reflux for 6h. After the reaction was completed, it was cooled to room temperature, the solvent was spun off, dichloromethane (100 mL) and deionized water (60 mL) were added, and the organic layer was separated. The organic layer was dried with anhydrous sodium sulfate and spun dry. Acetic anhydride (20 mL) was added thereto, and heated to reflux at 150° C. for 12 ...

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Abstract

The invention discloses a fluorine-containing pyrrole diphenylacerylene organic solid fluorescent compound and a synthetic method and application thereof. The compound is of the structure shown in the formula 1, wherein X is alkyl or alkoxy or aryl or azyl or substituted amino or hydrogen or trifluoromethyl, R1 is cyan or formyl group, and R2 is alkoxy or F. The synthetic method is simple and easy to implement, raw materials are easy to obtain, and the yield is high. The fluorine-containing pyrrole diphenylacerylene organic solid fluorescent compound has the high fluorescent strength, the high fluorescence quantum yield, long fluorescence service life, and good liquid crystal performance; the fluorescence strength, the light-emitting color, the fluorescence quantum yield, the viscosity, refractive indexes and other physical properties of the compound can be adjusted by changing a substituent group on a pyrrole ring, and the compound has the advantage that adjustment is easy and convenient.

Description

technical field [0001] The invention belongs to the field of organic solid fluorescent materials, in particular to a tolan organic solid fluorescent compound with fluorine-containing pyrrole (such as 2-cyano-3-ethoxy-4-fluoropyrrole) as the core structure and its synthesis The method and application, this kind of compound can effectively regulate its physical properties, fluorescence, liquid crystal and other properties by changing the substituent group on the fluorine-containing pyrrole or at the end of tolanyl acetylene. Background technique [0002] Fluorescent materials play a very important role in the research of sensors and photoelectric functional devices. Traditional fluorescent chromophores will weaken or even not emit light at high concentrations. This phenomenon is called "concentration quenching" effect. The main reason for concentration quenching is related to the formation of aggregates, so the solubility quenching effect is usually also called "aggregation-ca...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/36C07D207/34C09K11/06C09K19/34
CPCC07D207/34C07D207/36C09K11/06C09K19/3477C09K2211/1007C09K2211/1029
Inventor 曾卓朱德兆刘建晖
Owner SOUTH CHINA NORMAL UNIVERSITY
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