Aggregation-induced red light emission material and preparation method thereof

An aggregation-inducing and red-emitting technology, which is applied in the fields of luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of harsh reaction conditions, aggregation and quenching of organic red light materials, and high cost, and achieve mild reaction conditions and experimental The effect of simple steps

Inactive Publication Date: 2017-03-22
XIAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to provide an aggregation-induced red light emitting material to solve the problem of aggregation quenching of organic red light materials
[0006] The present invention further provides a method for preparing an aggregation-induced red light-emitting material. The method is aimed at the difficulty in synthesizing the existing aggregation-induced red light-emitting material, and the reaction conditions are harsh (anhydrous and oxygen-free, flammable butyl Lithium, etc.), high cost (raw materials, noble metal catalysts are expensive), etc., invented a method for the preparation of aggregation-induced red light-emitting materials with cheap and easy-to-obtain experimental raw materials and mild reaction conditions

Method used

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  • Aggregation-induced red light emission material and preparation method thereof
  • Aggregation-induced red light emission material and preparation method thereof
  • Aggregation-induced red light emission material and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0053] In a preferred technical solution of the present invention, R 1 is n-butyl, R 2 for -H.

[0054] (1) Synthesis of intermediate 1-(4-hydroxyphenyl)-1,2,2-triphenylethylene. 4-Hydroxybenzophenone (1.9 g, 10 mmol), benzophenone (2.2 g, 12 mmol), and Zn powder (2.9 g, 44 mmol) were added to a 250 mL round bottom flask. After vacuuming and changing nitrogen three times, 80 mL of tetrahydrofuran was added. After cooling to 0°C, slowly add TiCl 4 (4.2 g, 22 mmol), followed by stirring for 1 h. Then stir at 70°C for 24h, after cooling to room temperature, add 80mL of dilute hydrochloric acid (1mol / L) to adjust to neutrality, extract three times with DCM, collect the organic layer, dry over anhydrous magnesium sulfate, and spin the solvent to obtain the crude product. A 20:1 mixture of petroleum ether and ethyl acetate as eluent, SiO 2 As a stationary phase, 0.8 g of a white solid was obtained by column chromatography, and the yield was 47%.

[0055]

[0056] (2) Synth...

Embodiment 2

[0064] In another preferred technical solution of the present invention, R 1 is cyclohexyl, R 2 for -CH 3 .

[0065] (1) Synthesis of intermediate 4-(1,2-diphenyl-2-p-tolylvinyl)phenol. 4-Hydroxybenzophenone (1.9 g, 10 mmol), 4-methylbenzophenone (2.9 g, 15 mmol), and Zn powder (3.9 g, 60 mmol) were added to a 250 mL round bottom flask. After vacuuming and changing nitrogen three times, 80 mL of tetrahydrofuran was added. After cooling to 0°C, slowly add TiCl 4 (5.7g, 30mmol), followed by stirring for 0.8h. Then stir at 65°C for 36h, after cooling to room temperature, add 80mL of dilute hydrochloric acid (1mol / L) to adjust to neutrality, extract three times with DCM, collect the organic layer, dry over anhydrous magnesium sulfate, and spin the solvent to obtain the crude product. A 40:1 mixture of petroleum ether and ethyl acetate as eluent, SiO 2 As a stationary phase, 0.76 g of a white solid was separated by column chromatography, and the yield was 42%.

[0066]

...

Embodiment 3

[0073] In another preferred technical solution of the present invention, R 1 is 2-ethylhexyl, R 2 for-OCH 3 .

[0074] (1) Synthesis of intermediate 4-(2-(4-methoxyphenyl)-1,2-diphenylvinyl)phenol. Into a 250 mL round bottom flask were added 4-hydroxybenzophenone (1.9 g, 10 mmol), 4-methoxybenzophenone (2.1 g, 10 mmol), Zn powder (2.6 g, 40 mmol). After vacuuming and changing nitrogen three times, 80 mL of tetrahydrofuran was added. After cooling to 0°C, slowly add TiCl 4 (3.8g, 20mmol), then stirred for 1h, then stirred at 85°C for 12h, after cooling to room temperature, added 80mL of dilute hydrochloric acid (1mol / L) to adjust to neutral, extracted three times with DCM, collected the organic layer, anhydrous magnesium sulfate Drying, spin-drying solvent obtains crude product, is the eluent with the mixture of sherwood oil and ethyl acetate of 60:1 with the volume ratio, SiO 2 As a stationary phase, 0.87 g of a white solid was obtained by column chromatography, with a y...

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Abstract

The invention discloses an aggregation-induced red light emission material and a preparation method thereof. The aggregation-induced red light emission material has a general structural formula shown as a formula [I]. When the aggregation-induced red light emission material disclosed by the invention is prepared, firstly, a benzophenone derivative with a substituent group on a 4-site and 4-hydroxybenzophenone are synthesized into a tetraphenylethylene derivative with hydroxyl under the catalysis of zinc powder and titanium tetrachloride; secondly, a tetrachloroperyleneimide derivative is synthesized by using an organic amine and 1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic dianhydride; finally, the two intermediates are utilized to prepare a final product through a Williamson reaction. The preparation method of the aggregation-induced red light emission material, disclosed by the invention, has the advantages of mild conditions, simple process, low price of used raw materials and the like. The formula [I] is shown in the description.

Description

technical field [0001] The invention belongs to the technical field of organic aggregation-induced luminescence materials, and in particular relates to an aggregation-induced red luminescence material and a preparation method thereof. Background technique [0002] Organic red light materials are often large π organic red light materials are often planar molecules with large π-conjugated systems or π-conjugated molecules with push-pull electron groups, such as fused ring compounds, porphyrin derivatives, pyran Nitrile (DCM) dyes, boron dipyrrole (BODIPY) derivatives and benzothiadiazole-based dyes, etc. Although these molecules emit strong fluorescence in solution, in the aggregated state or in the solid state, due to the strong π-π stacking or dipole-dipole interaction between molecules, it is easy to form excimer associations between the same molecules. Excimers or exciplexes between different molecules, resulting in a decrease in fluorescence intensity (Nature, 1999, 397,...

Claims

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Application Information

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IPC IPC(8): C07D471/06C09K11/06
CPCC09K11/06C07D471/06C09K2211/1029
Inventor 赵秋丽
Owner XIAN UNIV OF SCI & TECH
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