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Preparation method of 1,3-diene derivatives with aggregation-induced luminescence properties

A technology of aggregation-induced luminescence and derivatives, which is applied in the preparation of organic compounds, condensation hydrocarbons with dehydrocarbons, luminescent materials, etc., can solve the problems of high cost and low efficiency, and achieve high efficiency, high reaction efficiency, The effect of avoiding waste

Inactive Publication Date: 2016-05-25
GUANGDONG OCEAN UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The purpose of the present invention is to address the deficiencies of the prior art, to provide a 1,3-diene derivative with aggregation-induced luminescence properties and a preparation method thereof, which has strong aggregation-induced luminescence properties, and its preparation It is obtained by oxidative dehydrogenation coupling reaction of olefins based on palladium catalyzed olefins as a reaction substrate; the method has the characteristics of mild reaction conditions, simple operation, easy availability of raw materials, high selectivity and environmental friendliness, and solves the problems in the prior art. The synthesis of such compounds with aggregation-induced luminescent properties has the disadvantages of low efficiency and high cost

Method used

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  • Preparation method of 1,3-diene derivatives with aggregation-induced luminescence properties
  • Preparation method of 1,3-diene derivatives with aggregation-induced luminescence properties
  • Preparation method of 1,3-diene derivatives with aggregation-induced luminescence properties

Examples

Experimental program
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Effect test

Embodiment 1

[0048] The preparation of 1,1,4,4-tetraphenyl-1,3-butadiene, the reaction formula is as follows:

[0049]

[0050] The preparation method is as follows:

[0051] (1) Add Pd(OAc) successively to the test tube 2 (12mg, 5mol%), N,N-dimethylformamide (2mL), benzyl chloride (126mg, 1.0equiv.), 1,1-diphenylethylene (180mg, 1.0mmol), and connected a balloon of one atmosphere of oxygen;

[0052] (2) Place the test tube containing the reaction mixture in an oil bath at 110°C and stir for 10 hours;

[0053] (3) After the completion of the reaction detected by TLC, cool to room temperature, add 10 mL of saturated brine to the reaction mixture for dilution, then extract with ethyl acetate (3×10 mL), combine the organic layers and wash with saturated brine, with anhydrous MgSO 4 Drying is carried out; the obtained organic phase is distilled off under reduced pressure to remove most of the solvent, and the target product can be obtained by preparative thin-layer chromatography.

[0...

Embodiment 2

[0056] The preparation of bromine-containing 1,1,4,4-tetrasubstituted-1,3-butadiene, the preparation method and the reaction formula are as follows:

[0057] (1) Synthesis of alkenes with the cross-coupling reaction of tosyl hydrazone and aryl or heteroaryl halide and the Wittig reaction, the reaction formula is as follows:

[0058]

[0059] (2) Using palladium to catalyze the self-oxidative dehydrogenation coupling reaction, the reaction formula is as follows:

[0060]

Embodiment 3

[0062] The bromine-containing 1,1,4,4-tetrasubstituted-1,3-butadiene prepared in Example 2 was prepared by Suzuki reaction to prepare 1,1,4,4-tetrasubstituted-1 containing aromatic groups ,3-butadiene derivatives.

[0063] Reaction formula:

[0064]

[0065] method:

[0066] (1) Add Pd(PPh 3 ) 4 (5mol%), K 2 CO 3 (2equiv), bromine-containing 1,1,4,4-tetrasubstituted-1,3-butadiene (1.0mmol), add toluene and water mixed solvent (volume ratio is 3:1), and stir at room temperature for 30 minutes, Then add arylboronic acid (4.2 equiv);

[0067] (2) Place the test tube containing the reaction mixture in a 90°C oil bath and stir for 20 hours;

[0068] (3) After the completion of the reaction detected by TLC, cool to room temperature, add 10 mL of saturated brine to the reaction mixture for dilution, then extract with ethyl acetate (3×10 mL), combine the organic layers and wash with saturated brine, with anhydrous MgSO 4 Drying is carried out; the obtained organic phase is...

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Abstract

The invention discloses a preparation method of a 1,3-diene derivative having aggregation-induced emission property and belongs to the technical field of synthesis of compounds. The derivatives have strong aggregation-induced emission property and the preparation of the derivatives is achieved by carrying out oxydehydrogenation coupling reaction on a substrate olefin under the catalysis of palladium in the presence of oxygen serving as an oxidant. The method has the characteristics of mild reaction condition, simple operation, use of easily available raw materials, high selectivity and environmental friendliness and is used for solving the deficiencies in the prior art that the synthetic efficiency of the compounds having the aggregation-induced emission property is low and the cost is high.

Description

technical field [0001] The invention relates to a preparation method of 1,3-diene derivatives, in particular to a preparation method of 1,3-diene derivatives with aggregation-induced luminescence properties, and belongs to the technical field of chemical substance synthesis. Background technique [0002] Aggregation-Induced Emission (AIE) refers to the phenomenon that a class of molecules that do not emit light in the solution emit light in an aggregated state. The proposal of the AIE phenomenon has opened up a new perspective for people to understand organic light-emitting materials. The AIE phenomenon and The discovery and research of AIE compounds provide a fundamental solution to the problems brought about by the common fluorescent compound ACQ in the practical application process, and provide a new idea for the design of solid-state materials with high fluorescence quantum yields. [0003] The special fluorescence enhancement phenomenon of organic fluorescent compounds ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C15/50C07C2/84C07C25/24C07C17/269C07C39/21C07C37/16C09K11/06C07C59/68C07C51/02C07C69/78C07C67/14
Inventor 温燕梅邓春梅康信煌吴育廉
Owner GUANGDONG OCEAN UNIVERSITY
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