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9, 10-dipyrrolyl anthracene fluorescent compound as well as preparation method and application thereof

A fluorescent compound and compound technology, used in chemical instruments and methods, fluorescence/phosphorescence, luminescent materials, etc., can solve the synthesis and properties of asymmetric 9,10-thienyl anthracene compounds. No literature and patent reports have been reported, etc. problem, to achieve the effect of good cell staining function, simple synthesis and great application prospects

Pending Publication Date: 2020-07-14
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, the synthesis and properties of asymmetric 9,10-thienylanthracene compounds with AIE properties have not been reported in any literature and patents

Method used

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  • 9, 10-dipyrrolyl anthracene fluorescent compound as well as preparation method and application thereof
  • 9, 10-dipyrrolyl anthracene fluorescent compound as well as preparation method and application thereof
  • 9, 10-dipyrrolyl anthracene fluorescent compound as well as preparation method and application thereof

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preparation example Construction

[0050] The present invention provides a method for preparing the asymmetric 9,10-bisthienylanthracene aggregation-induced light-emitting compound described in the above scheme, comprising the following steps:

[0051] (i) when R is CN in formula I, the compound shown in formula I is 9-thienyl-10-(5-cyanothiophene) anthracene (TCTA), and preparation method comprises the following steps:

[0052] (1) Under a protective atmosphere, mix 9,10-dibromoanthracene, 2-thiopheneboronic acid, a palladium catalyst, a basic compound and a solvent for a Suzuki coupling reaction to obtain 9-thienyl-10-bromoanthracene; The molar ratio of 9,10-dibromoanthracene and 2-thiopheneboronic acid is 1:1~1.2;

[0053] (2) Under protective atmosphere, 9-thienyl-10-bromoanthracene, 2-cyano-5-boronic acid thiophene, palladium catalyst, basic compound and solvent are mixed for Suzuki coupling reaction to obtain 9-thienyl- 10-(5-cyanothiophene)anthracene; the molar ratio of 2-cyano-5-boronic acid thiophene ...

Embodiment 1

[0094] Preparation of 9-thienyl-10-(5-thienylcyano)anthracene (TCTA):

[0095] (1) Preparation of 9-thienyl-10-bromoanthracene:

[0096] Under nitrogen protection, 9,10-dibromoanthracene (3.36g, 10mmol) and Pd(PPh 3 ) 4 (10mol%) was dissolved in 80.0mLTHF, after stirring for 30min, 2-thiopheneboronic acid (2.10 g, 10.0mmol) was added and the concentration was 5.0equiv.Na 2 CO 3 Solution 60mL, heated to reflux for 12 h, stopped the reaction, cooled to room temperature. The solvent was removed by rotary evaporation, extracted with dichloromethane, the organic phases were combined, and dried over anhydrous magnesium sulfate. After suction filtration, the filtrate was rotary evaporated to remove the solvent, and separated by column chromatography using petroleum ether as the eluent to obtain a white solid (2.80 g, 6.6 mmol), yield: 66%.

[0097] (2) Preparation of 9-thienyl-10-(5-cyanothiophene) anthracene:

[0098] Under nitrogen protection, 9-thienyl-10-bromoanthracene (0...

Embodiment 2

[0101] Preparation of 9-thienyl-10-(5-hydroxythiophene)anthracene (THTA):

[0102] (1) Preparation of 9-thienyl-10-bromoanthracene:

[0103] Under nitrogen protection, 9,10-dibromoanthracene (3.36g, 10mmol) and Pd(PPh 3 ) 4 (10mol%) was dissolved in 80.0mLTHF, after stirring for 30min, 2-thiopheneboronic acid (2.10 g, 10.0mmol) was added and the concentration was 5.0equiv.Na 2 CO 3 Solution 60mL, heated to reflux for 12 h, stopped the reaction, cooled to room temperature. The solvent was removed by rotary evaporation, extracted with dichloromethane, the organic phases were combined, and dried over anhydrous magnesium sulfate. After suction filtration, the filtrate was rotary evaporated to remove the solvent, and separated by column chromatography using petroleum ether as the eluent to obtain a white solid (2.80 g, 6.6 mmol), yield: 66%.

[0104] (2) Preparation of 9-thienyl-10-(5-formylthiophene)anthracene:

[0105] Under nitrogen protection, 9-thienyl-10-bromoanthracen...

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Abstract

The invention relates to the technical field of aggregation-induced emission materials, and provides an asymmetric 9, 10-dithienyl anthracene compound fluorescent compound has a structure shown as a formula I, and 9-thiophenyl-10-(5-cyanothiophene)anthracene(TCTA), 9-thiophenyl-10-(5-hydroxythiophene)anthracene(THTA) and 9-thiophenyl-10-(5-thiophenamide)anthracene (TATA) have remarkable aggregation-induced emission characteristics. The preparation method of the compound provided by the invention has the advantages of simple steps, low cost, milder preparation conditions, suitability for industrial production and great application prospect. The invention also provides an application of the asymmetric 9,10-dithienyl anthracene compound fluorescent compound in cell fluorescence imaging and organic photoluminescence materials.

Description

technical field [0001] The invention relates to the technical field of aggregation-induced luminescent materials, in particular to an asymmetric 9,10-bisthienylanthracene fluorescent compound and its preparation method and application. Background technique [0002] In the past few years, due to the wide variety, good adjustability, rich colors, high color purity, and relatively flexible molecular design, organic light-emitting materials have been paid more and more attention in the field of light-emitting. However, the efficiency of traditional luminescent materials usually becomes very poor in the aggregated state, such as aggregation-induced fluorescence quenching (Anti-aggregation-caused quenching, ACQ) in the solid state due to aggregation. This phenomenon has become a major obstacle for the application of organic luminophores, especially in microscopic imaging and biosensing. In 2001, the team of Academician Tang Benzhong accidentally discovered a class of molecules wi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/16C07D333/38C09K11/06G01N21/64H01L51/50H01L51/54
CPCC07D333/38C07D333/16C09K11/06G01N21/6428G01N21/6456C09K2211/1092C09K2211/1011G01N2021/6439H10K85/655H10K85/615
Inventor 王仁杰蒲守智张洁刘刚
Owner JIANGXI SCI & TECH NORMAL UNIV