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Asymmetric 9,10-dithienylanthracene fluorescence compound, and preparation method and application thereof

A bisthienyl anthracene and fluorescent compound technology, applied in chemical instruments and methods, fluorescence/phosphorescence, hydroxyanthraquinone dyes, etc., can solve the problem of rare AIE compound molecules, and achieve simple preparation methods, low preparation costs, and high preparation conditions mild effect

Active Publication Date: 2019-08-23
豫章师范学院
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  • Abstract
  • Description
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Problems solved by technology

However, so far, there are very few reports on AIE compound molecules modified by benzoxazole and benzothiazole in this field.

Method used

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  • Asymmetric 9,10-dithienylanthracene fluorescence compound, and preparation method and application thereof
  • Asymmetric 9,10-dithienylanthracene fluorescence compound, and preparation method and application thereof
  • Asymmetric 9,10-dithienylanthracene fluorescence compound, and preparation method and application thereof

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preparation example Construction

[0057] The present invention provides a preparation method for the asymmetric 9,10-bisthienylanthracene fluorescent compound described in the above scheme, comprising the following steps:

[0058] (i) When R in formula I is , the compound shown in formula I is [9-thienyl, 10-(5-formyl-2-thienyl)] anthracene, and the preparation method comprises the following steps:

[0059] (1) Under a protective atmosphere, mix 9,10-dibromoanthracene, thiophene-2-boronic acid, a palladium catalyst, a basic compound and a solvent for a Suzuki coupling reaction to obtain 9-bromo-10-thienylanthracene;

[0060] (2) Under protective atmosphere, 9-bromo-10-thienyl anthracene, 5-formyl-2-thiophene boronic acid, palladium catalyst, basic compound and solvent are mixed for Suzuki coupling reaction to obtain [9-thienyl , 10-(5-formyl-2-thienyl)]anthracene.

[0061] In the present invention, the reaction equation of the Suzuki coupling reaction in the step (1) is as shown in formula V:

[0062]

...

Embodiment 1

[0102] Preparation of [9-thienyl,10-(5-formyl-2-thienyl)]anthracene (DTA-F)

[0103] (1) Preparation of 9-bromo-10-thienyl anthracene:

[0104] Under nitrogen protection, 9,10-dibromoanthracene (1.00g, 3.0mmol) and Pd(PPh 3 ) 4 (0.10g) was dissolved in 80.0mLTHF, after stirring for 30min, thiophene-2-boronic acid (0.46g, 3.6mmol) was added and the concentration was 2.0mol / L Na 2 CO 3 Solution 30.0mL, heated to reflux for 12h, stop 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. Suction filtration, the filtrate was rotary evaporated to remove the solvent, and petroleum ether was used as the eluent for column chromatography to obtain a yellow-green solid with a yield of 50%.

[0105] (2) Preparation of [9-thienyl, 10-(5-formyl-2-thienyl)]anthracene (DTA-F):

[0106] Under nitrogen protection, 9-bromo-10-thienylanthracene (1....

Embodiment 2

[0109] Preparation of [9-thienyl, 10-(5-vinylbenzothiazolyl)-2-thienyl]anthracene (DTA-BT):

[0110] Under the protection of nitrogen, potassium tert-butoxide (0.67g, 0.6mmol) and 10.0mL THF were reacted at 0°C for 10min, then 2-methylbenzothiazole (0.07g, 0.45mmol) was dissolved in 8.0mL THF Slowly drop the mixed solution and keep the temperature at 0°C for 1.0h. Then [9-thienyl, 10-(5-formyl-2-thienyl)] anthracene (DTA-F, 0.11g, 0.3mmol) was dissolved in 8.0mL THF, slowly added dropwise, and reacted for 1.0h. After the reaction is complete, add water to terminate the reaction, extract with dichloromethane, combine the organic phases, and dry over anhydrous magnesium sulfate. After suction filtration, the filtrate was rotary evaporated to remove the solvent, and separated by column chromatography using petroleum ether: ethyl acetate = 10:1 as the eluent to obtain a yellow solid with a yield of 50%.

[0111] Structure Identification: 1 H NMR(400MHz,DMSO,ppm):δ7.34(d,1H,thio...

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Abstract

The invention relates to the technical field of aggregation-induced luminescent materials, and provides an asymmetric 9,10-dithienylanthracene fluorescence compound. [9-thienyl,10-(5-vinylbenzothiazolyl)-2-thienyl]anthracene (DAT-BT) and [9-thienyl, 10-(5-vinylbenzoxazolyl)-2-thienyl]anthracene (DAT-BO) have significant AIE characteristics and a significant mechanical grinding discoloration characteristic. The invention also provides a preparation method of the compound. The preparation method provided by the invention has the advantages of simple steps, low cost, mild preparation conditions,suitableness for industrial production, and great application prospect. The invention further provides applications of the asymmetric 9,10-dithienylanthracene fluorescence compound in cell fluorescence imaging, organic photoluminescence materials and mechanical photochromic materials.

Description

technical field [0001] The invention relates to the technical field of aggregation-induced luminescent materials, in particular to a 9,10-bisthienylanthracene fluorescent compound and its preparation method and application. Background technique [0002] Organic light-emitting materials have broad application prospects in data storage, sensors, optical switches, organic light-emitting diodes (OLEDs) and organic light-emitting transistors (OLETs), and are currently a major research hotspot in the field of optical functional materials. Generally speaking, due to the influence of exciton coupling or formation of substances such as excimers and exciplexes, the luminescence efficiency of most organic light-emitting compound molecules in the solid state is significantly weaker than that in the solution . At the beginning of the new century, academician Tang Benzhong of the Hong Kong University of Science and Technology reported a new class of hexaphenylsilole organic light-emittin...

Claims

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Application Information

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IPC IPC(8): C07D333/22C07D417/14C07D413/14C09B1/00C09K9/02C09K11/06G01N21/64
CPCC07D333/22C07D413/14C07D417/14C09B1/02C09K9/02C09K11/06C09K2211/1011C09K2211/1033C09K2211/1037C09K2211/1092G01N21/6428
Inventor 蒲守智王仁杰刘刚刁璐
Owner 豫章师范学院
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