Aggregation-induced red light emission material and preparation method thereof

An aggregation-inducing and red-emitting technology, which is applied in the direction of luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problems that the final product is not 100% pure and difficult to separate, and achieves mild reaction conditions, easy purification, Experimental effect of cheap raw materials

Inactive Publication Date: 2017-03-29
XIAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, many tetraphenylethylene derivatives are a mixture of cis-isomers and trans-isomers, which are difficult to separate, resulting in final products that are not 100% pure in configuration (Chem. Sci.2012,3,493-497; J.Am.Chem.Soc.2012,134,9956-9966)
[0004] Perylene imides are a class of traditional organic red-emitting materials, but there are serious ACQ effects

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

[0052] In a preferred technical solution of the present invention, R 1 is n-butyl, R 2 for -H.

[0053] (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%.

[0054]

[0055] (2) Synth...

Embodiment 2

[0063] In another preferred technical solution of the present invention, R 1 is cyclohexyl, R 2 for -CH 3 .

[0064] (1) Synthesis of intermediate 4-(1-phenyl-2,2-xylylvinyl)phenol. 4-Hydroxybenzophenone (1.9g, 10mmol), 4,4'-dimethylbenzophenone (3.2g, 15mmol), and Zn powder (3.9g, 60mmol) were added to a 250mL 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, 0.62 g of a white solid was obtained by column chromatography, with a yield of 32%.

[0065]

[0066] (...

Embodiment 3

[0072] In another preferred technical solution of the present invention, R 1 is n-octyl, R 2 for-OC 2 h 5 .

[0073] (1) Synthesis of intermediate 4,4'-diethoxybenzophenone. Add bromoethane (8.1g, 75mmol) and 4,4'-dihydroxybenzophenone (5.4g, 25mmol) into a three-necked flask, add 200mL of acetone, and then add potassium carbonate (10.4g, 75mmol), Then the temperature was raised to 55°C and stirring was continued for 36h. After the reaction stopped, cool to room temperature, filter, collect the filtrate, and dry the solvent by rotary evaporation to obtain the crude product, using a mixture of petroleum ether and ethyl acetate with a volume ratio of 40:1 as the eluent, SiO 2 As a stationary phase, 5.5 g of 4,4'-diethoxybenzophenone was obtained after separation and purification by column chromatography, with a yield of 81%.

[0074]

[0075] (2) Synthesis of intermediate 4-(2,2-bis(4-ethoxyphenyl)-1-phenylvinyl)phenol. Into a 250 mL round bottom flask were added 4-hyd...

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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 structural formula represented by the formula [I]. The aggregation-induced red light emission material is prepared by the following steps: using diphenylmethanone derivatives and 4-hydroxyl diphenylmethanone, which have same groups on the 4,4'- positions, to synthesize tetraphenyl ethylene derivatives with hydroxyl groups in the presence of zinc powder and titanium tetrachloride; then using organic amine and 1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic acid dianhydride to synthesize tetrachloroperylene imide derivatives; and finally preparing the final product from the two intermediates through Williamson reactions. The provided preparation method has the advantages of mild conditions, simple technology, easy purification, and cheap raw materials.

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] Red light materials have excellent properties. For example, red-near-infrared fluorescent dyes can be excited by visible light sources, and compared with ultraviolet light, they are less harmful to organisms; The specific location of the lesion can be determined conveniently; the red-near-infrared light probe can avoid the interference of biological tissue autofluorescence. In addition to the above advantages, organic red light-emitting materials also have the characteristics of various types, easy modification, and various structures. However, organic red light-emitting materials are often large π organic red light-emitting materials are often planar molecules with large π-conjugated systems or π-conjugated molec...

Claims

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Application Information

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