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Preparation method for 4-(9-(beta-naphthaline)-10-anthryl) ethyl benzoate

A technology of ethyl benzoate and ethyl bromobenzoate is applied in the preparation of carboxylic acid esters, the preparation of organic compounds, chemical instruments and methods, etc., and can solve problems such as unfavorable construction of large-area devices, poor solubility, and complicated operations, Achieve the effect of low cost of raw materials, mild reaction conditions and safe experimental operation

Inactive Publication Date: 2017-01-11
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, many reported blue-light materials based on anthracene monomers have poor solubility, and electroluminescent devices must be constructed by vacuum evaporation film formation. The vacuum evaporation method has many disadvantages, such as: a large amount of waste of materials, high cost, and complicated operation. , which is not conducive to the construction of large-area devices, etc.

Method used

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  • Preparation method for 4-(9-(beta-naphthaline)-10-anthryl) ethyl benzoate
  • Preparation method for 4-(9-(beta-naphthaline)-10-anthryl) ethyl benzoate
  • Preparation method for 4-(9-(beta-naphthaline)-10-anthryl) ethyl benzoate

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Experimental program
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Embodiment 1

[0032] (1) Synthesis of 9-(β-naphthalene)-10-anthraceneboronic acid

[0033] Add 3.82g of 9-(β-naphthalene)-10-bromoanthracene to a 250mL reaction flask, then vacuumize and fill the reaction flask with nitrogen three times, add tetrahydrofuran, cool to -78°C, and slowly add 4.80mL of Butyllithium (2.5M inhexane) was added dropwise for half an hour. After stirring for 1 hour, 2.44 g of triisopropyl borate was added. After 20 minutes, the dropwise addition was completed. Return to room temperature and stir overnight. Add 30mL of 2mol / L hydrochloric acid, continue stirring for 1h, and extract with dichloromethane three times. The organic phase was dried with anhydrous magnesium sulfate, suction filtered, spin-dried, the crude product was heated to reflux in petroleum ether, filtered while hot to obtain the white target product 9-(β-naphthalene)-10-anthracenboronic acid (2.78g, 80% ).

[0034] (2) Synthesis of ethyl 4-(9-(β-naphthalene)-10-anthracenyl)benzoate

[0035] Add 2.26...

Embodiment 2

[0037] (1) Synthesis of 9-(β-naphthalene)-10-anthraceneboronic acid

[0038]Add 3.82g of 9-(β-naphthalene)-10-bromoanthracene to a 250mL reaction flask, then vacuumize and fill the reaction flask with nitrogen three times, add tetrahydrofuran, cool to -78°C, and slowly add 5.20mL of Butyllithium (2.5M inhexane) was added dropwise for half an hour. After stirring for 1 hour, 2.82 g of triisopropyl borate was added. After 20 minutes, the dropwise addition was completed, returned to room temperature, and stirred overnight. Add 30mL of 2mol / L hydrochloric acid, continue stirring for 1h, and extract with dichloromethane three times. The organic phase was dried with anhydrous magnesium sulfate, suction filtered, spin-dried, the crude product was heated to reflux in petroleum ether, filtered while hot to obtain the white target product 9-(β-naphthalene)-10-anthracenboronic acid (2.92g, 84% ).

[0039] (2) Synthesis of ethyl 4-(9-(β-naphthalene)-10-anthracenyl)benzoate

[0040] Add...

Embodiment 3

[0042] (1) Synthesis of 9-(β-naphthalene)-10-anthraceneboronic acid

[0043] Add 3.82g of 9-(β-naphthalene)-10-bromoanthracene to a 250mL reaction flask, then vacuumize and fill the reaction flask with nitrogen three times, add tetrahydrofuran, cool to -78°C, and slowly add 5.0mL of Butyllithium (2.5M inhexane) was added dropwise within half an hour. After stirring for 1 hour, 2.63 g of triisopropyl borate was added. After 20 minutes, the dropwise addition was completed, returned to room temperature, and stirred overnight. Add 30mL of 2mol / L hydrochloric acid, continue stirring for 1h, and extract with dichloromethane three times. The organic phase was dried with anhydrous magnesium sulfate, suction filtered, spin-dried, the crude product was heated to reflux in petroleum ether, filtered while hot to obtain the white target product 9-(β-naphthalene)-10-anthracenboronic acid (2.85g, 82% ).

[0044] (2) Synthesis of ethyl 4-(9-(β-naphthalene)-10-anthracenyl)benzoate

[0045] ...

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Abstract

The invention relates to a preparation method for 4-(9-(beta-naphthaline)-10-anthryl) ethyl benzoate. The preparation method comprises the steps that 9-(beta-naphthaline)-10-bromoanthracene is added in a reaction vessel, and solvent is added, when the temperature is reduced to -78 DEG C under nitrogen atmosphere, n-butyllithium is added and stirred, and triisopropyl borate is further added, then stirring is performed at normal temperature, and 9-(beta-naphthaline)-10-anthraceneboronic acid is obtained after being acidized with hydrochloric acid; the 9-(beta-naphthaline)-10-anthraceneboronic acid and 4-ethyl bromobenzoate are added in the reaction vessel, and catalyst and acid-binding agent are added, after vacuum pumping and nitrogen circulation, the solvent is added in the vessel, then all the materials react at the boiling point of the solvent, and column chromatography separation is performed to obtain the target product. The preparation method has the advantages of being low in material cost, mild in reaction conditions, and laying the foundation for building more blue-luminescent materials with excellent performances, and providing more possibilities for the research on that anthracene compounds serving as semiconducting materials are applied to organic electroluminescence devices, organic photoconductors and the like.

Description

technical field [0001] The invention belongs to the field of synthetic chemistry, and in particular relates to a preparation method of ethyl 4-(9-(β-naphthalene)-10-anthracenyl)benzoate. Background technique [0002] Anthracene is an important blue-light material in organic electroluminescence. It has high quantum efficiency, thermal stability, chemical stability, and easy derivatization. It has been widely studied by chemists. In 1963, Pope et al. observed luminescence by applying a voltage of 400V to an anthracene single crystal. Kodak's research team published a derivative based on 9,10-bis(β-naphthalene)anthracene (ADN). ADN has high efficiency in both solution and solid state, and is currently widely used. Among them, the two naphthalenes of 9,10-bis(β-naphthalene)anthracene and anthracene are in a vertical relationship, and the non-planar structure reduces the degree of intermolecular π-π stacking, which is beneficial to suppress concentration quenching. Compared wit...

Claims

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Application Information

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IPC IPC(8): C07C67/343C07C69/76C09K11/06
CPCC07C67/343C07F5/025C09K11/06C09K2211/1007C09K2211/1011C07C69/76
Inventor 李祥高孙炜肖殷王世荣
Owner TIANJIN UNIV
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