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Tetraborate intermediate for photoelectric material synthesis and preparation method of tetraborate intermediate

A technology of tetraborate and optoelectronic materials, which is applied in chemical instruments and methods, compounds containing elements of Group 3/13 of the periodic table, organic chemistry, etc., and can solve the problems of complex steps and long synthetic routes of macromolecules.

Pending Publication Date: 2021-05-11
NANJING UNIV OF POSTS & TELECOMM
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Problems solved by technology

[0005] Technical problem: The object of the present invention is to provide a tetraborate intermediate for the synthesis of photoelectric materials and its preparation method, which solves the problem of long synthesis routes and complicated steps for macromolecules, and provides a solution for the preparation of multi-armed macromolecules and dendrimers. Provide solutions for compounds and provide a technical basis for expanding the application of compounds based on star monomers containing four active sites in the field of optoelectronics

Method used

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  • Tetraborate intermediate for photoelectric material synthesis and preparation method of tetraborate intermediate
  • Tetraborate intermediate for photoelectric material synthesis and preparation method of tetraborate intermediate
  • Tetraborate intermediate for photoelectric material synthesis and preparation method of tetraborate intermediate

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example 1

[0032] Example 1: Preparation of spirofluorene tetraborate

[0033] Under nitrogen, 2,2',7,7'-tetrabromospirofluorene (1.26 g, 2.0 mmol), pinacol diboronate (3.05 g, 12.0 mmol), potassium acetate (1.88 g, 18.0 mmol) were combined ) and 1,4-dioxane (30mL) were added to a 100mL reaction flask, followed by Pd (dppf 2 ) 2 (0.30 g, 0.4 mmol) catalyst, reacted at 100 °C overnight. The reaction was quenched with ice water, the organic phase was extracted with dichloromethane, washed two or three times with deionized water, dried over anhydrous magnesium sulfate, and filtered with suction. The crude product was concentrated in vacuo, and purified by column chromatography (eluent is DCM) to obtain 0.95 g of spirofluorene tetraborate as a white solid with a yield of 58%.

[0034] like figure 1 , 2 shown, 1 H NMR (400MHz, CDCl 3 ,δ): 7.85(s, 8H), 7.09(s, 4H), 1.25(s, 48H). 13 C NMR: (100MHz, CDCl 3 ,δ): 148.22, 144.73, 134.58, 130.48, 128.86, 119.71, 83.69, 65.91, 24.81.

example 2

[0035] Example 2: Preparation of pyrene tetraborate

[0036] Under nitrogen, 1,3,6,8-tetrabromopyrene (1.20 g, 2.3 mmol), pinacol diboronate (3.50 g, 13.8 mmol), potassium acetate (1.98 g, 20.0 mmol) and 1 ,4-dioxane (30mL) was added to a 100mL reaction flask, followed by Pd (dppf 2 ) 2 (0.30 g, 0.4 mmol) catalyst, reacted at 100 °C overnight. The reaction was quenched with ice water, the organic phase was extracted with dichloromethane, washed two or three times with deionized water, dried over anhydrous magnesium sulfate, and filtered with suction. The crude product was concentrated in vacuo, and purified by column chromatography (eluent is DCM) to obtain pyrene tetraborate as a yellow solid, 0.76 g, in a yield of 47%.

[0037] like image 3 , 4 shown, 1 H NMR (400MHz, CDCl 3 ,δ): 9.16(s, 4H), 8.99(s, 2H), 1.50(s, 48H). 13 C NMR (100MHz, CDCl 3 ,δ): 141.32, 141.31, 137.97, 129.41, 123.98, 83.82, 25.09.

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Abstract

The invention discloses a tetraborate intermediate for photoelectric material synthesis and a preparation method of the tetraborate intermediate. The intermediate is prepared by taking an organic light-emitting monomer and bis(pinacolato)diboron as raw materials through a palladium-catalyzed coupling reaction. The innovation of the invention lies in that the intermediate monomer tetraborate which can be used in the fields of organic photoelectrons and flexible electronics is synthesized in a chemical coupling manner for the first time; the tetraborate compound can be used as an intermediate for preparing a photoelectric material, and effectively solves the problems of poor solubility of a monomer and long synthetic route of the photoelectric material; and the tetraborate intermediate plays a very important role in expanding the application of the material compounds in the field of photoelectric materials.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, in particular to a tetraborate intermediate used for photoelectric material synthesis and a preparation method thereof, and several tetraborate intermediates are protected by patent. Background technique [0002] As a very important material type, macromolecules have extremely important application prospects in the field of organic semiconductors. At the same time, the synthetic steps of macromolecular materials are relatively complex and the route is too long, which poses a great challenge to chemists. Therefore, research on synthetic methods for macromolecular materials has always been the focus of scientists and R&D personnel. A common type of macromolecular synthesis in the field of organic semiconductors is achieved by Suzuki coupling. In the early stage, our research group also explored the research on the synthesis method of macromolecules assisted by microwave, which ...

Claims

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Application Information

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IPC IPC(8): C07F5/02
CPCC07F5/025
Inventor 赖文勇江翼黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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