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Aggregation-induced red light-emitting material and preparation method thereof

An aggregation-induced, red-emitting technology, applied in 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 expensive, and achieve mild reaction conditions and experimental results. Step-by-step effect

Inactive Publication Date: 2018-11-13
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-emitting material and preparation method thereof
  • Aggregation-induced red light-emitting material and preparation method thereof
  • Aggregation-induced red light-emitting 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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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/06C09K11/06
CPCC07D471/06C09K11/06C09K2211/1029
Inventor 赵秋丽
Owner XIAN UNIV OF SCI & TECH
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