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Polysubstituted acene derivative and preparation thereof

A technology of benzene derivatives and multi-substitution, applied in the field of multi-substituted acene derivatives and preparation thereof, can solve the problems of increased operation complexity, unstable preparation, cumbersome steps and the like, and achieves mild conditions, simple process and easy operation. Effect

Inactive Publication Date: 2008-10-08
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the former step of the above synthesis method is cumbersome, or involves the synthesis of multiple complex intermediates, or needs to use expensive zirconocene dichloride, which first prepares an unstable cyclopentadiene zirconocene intermediate, Increases the complexity of the operation and is only used for the preparation of aryl or alkyl substituted acene derivatives

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  • Polysubstituted acene derivative and preparation thereof
  • Polysubstituted acene derivative and preparation thereof
  • Polysubstituted acene derivative and preparation thereof

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preparation example Construction

[0022] The preparation method of multi-substituted acene derivatives of the present invention is as follows:

[0023] Stir and react 1,2-disubstituted acetylene derivatives with a certain amount of reducing agent in an organic solvent for 1 minute to 36 hours, and the reaction temperature is -78°C to 50°C; then, add polyhalogenated benzene derivatives and stir the reaction From 1 minute to 36 hours, the reaction temperature is -78°C to 50°C; finally, the reaction is quenched with water, an aqueous inorganic salt solution, or acid, and the target product is obtained by separation and purification.

[0024] By simply adjusting the ratio between 1,2-disubstituted acetylene derivatives and polyhalogenated benzene derivatives, "asymmetry" (such as Examples I, IV, V) or "symmetry" (such as Examples II, III, VI) reaction product of structure. When the ratio between polyhalogenated benzene derivatives and 1,2-disubstituted acetylene derivatives is greater than or equal to 1:2, it is ...

Embodiment 1、1

[0028] Embodiment 1, 1,2,3,4-tetrafluoro-5,6,7,8-tetraphenylnaphthalene (1,2,3,4-tetrafluoro-5,6,7,8-tetraphenylnaphthalene, I) preparation of

[0029] Take a 50ml two-necked flask, add lithium (18mg, 2.63mmol), naphthalene (0.89g, 2.65mmol), tetrahydrofuran (5ml), stir and react at 25°C for 4 hours to obtain a naphthalenelithium solution. To this solution was added a solution of tolanylacetylene (0.31g, 1.75mmol) in tetrahydrofuran (2ml) at 25°C, and the reaction was stirred for 20 minutes, then hexafluorobenzene (0.40g, 2.17mmol) was added, stirred for 1 hour, and then Add 1 ml of saturated aqueous ammonium chloride solution and stir for 5 minutes to stop the reaction. Extracted with ether, dried over anhydrous magnesium sulfate, and rotary evaporated under reduced pressure, the obtained crude product was treated with SiO 2 Column chromatography (petroleum ether rinse at 60-90°C), and recrystallization (tetrahydrofuran / ethanol) purified to obtain 131 mg (0.26 mmol) of the ...

Embodiment 2、9

[0032] Example 2, 9,10-difluoro-1,2,3,4,5,6,7,8-octaphenylanthracene (9,10-difluoro-1,2,3,4,5,6, 7,8-octaphenylanthracenel, II) Preparation

[0033] Take a 50ml two-necked flask, add lithium (104mg, 15.04mmol), naphthalene (1.92g, 14.96mmol), tetrahydrofuran (8ml), and stir at 25°C for 4 hours to obtain a naphthalenelithium solution. To this solution was added a solution of tolanylacetylene (1.78g, 9.98mmol) in tetrahydrofuran (4ml) at 25°C, and the reaction was stirred for 15 minutes, then hexafluorobenzene (0.46g, 2.49mmol) was added, stirred for 1 hour, and then Add 1 ml of saturated aqueous ammonium chloride solution and stir for 5 minutes to stop the reaction. Extracted with dichloromethane, dried over anhydrous magnesium sulfate, and rotary evaporated under reduced pressure, the obtained crude product was purified by recrystallization (dichloromethane / n-hexane, 3 / 1) to obtain product 0.41g (0.50mmol), and the yield was 20 %.

[0034] Melting point: >300°C

[0035] HR...

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Abstract

The invention discloses a polysubstituted acene derivate and a method for the production thereof. The polysubstituted acene derivate provided by the invention has the structure as the formula I, where, R<1>, R<2> and R<3> are the same or different and are halogen, alkyl, an aryl group or a trialkyl silicone base; and n is an integral number between 0 and 10. The polysubstituted acene derivate of the invention can be applied to fields such as organic electroluminescence, organic field effect transistor, organic solar battery, nonlinear optics and laser, and the method for the production thereof adopts the in-one-pot method with simple process, mild condition and easy operation.

Description

technical field [0001] The invention relates to a polysubstituted acene derivative and a preparation method thereof. Background technique [0002] Acene derivatives represented by anthracene, tetracene, pentacene, etc. have broad application prospects in the preparation of organic electroluminescent devices and organic field effect transistors (Appl. Phys. Lett., 2002, 80 , 2925; Angew.Chem., Int.Ed, 2001, 40, 1037; Appl.Phys.Lett., 2004, 85, 3357); Among them, the multi-substituted acene compounds have been researched because of their unique structural characteristics Our attention [Chem.Rev., 2006, 4809]. The parent structure is the same, and the structure and properties of the substituents can be changed to obtain materials with different electronic structure characteristics, different spatial arrangements, and thus different properties. [0003] Carrying out cycloaddition by aryne derivatives and furan derivatives, and then reducing cycloaddition products is the most c...

Claims

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Application Information

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IPC IPC(8): C07C17/26C07C25/22C07F7/08
Inventor 徐彩虹李书宏梅雪凝
Owner INST OF CHEM CHINESE ACAD OF SCI
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