Preparation method and application of condensed ring furan-based small-molecular material

A small molecule and furan technology is applied in the field of preparation of small molecule materials based on fused-ring furan, which can solve the problems of high reaction temperature, low practical value, time-consuming and laborious, and achieve mild reaction conditions, cheap catalytic system, and shortened reaction time. Effect

Inactive Publication Date: 2017-06-23
UNIVERSITY OF CHINESE ACADEMY OF SCIENCES
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The method yield is high, but needs to use equivalent water-sensitive n-butyllithium, anhydrous zinc chloride, also needs to use anhydrous solvent, and reaction temperature is higher (120 o c)
In addition, n-butyllithium is particularly dangerous, so its practical value is low
[0012] To sum up, the problems existing in the existing techniques for synthesizing fused-ring ...

Method used

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  • Preparation method and application of condensed ring furan-based small-molecular material
  • Preparation method and application of condensed ring furan-based small-molecular material
  • Preparation method and application of condensed ring furan-based small-molecular material

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preparation example Construction

[0036] like figure 1 As shown, the preparation method based on the fused ring furan small molecule material provided by the embodiment of the present invention comprises the following steps:

[0037] S101: Using 2,3-dibromofuran, 2,3-dibromothiophene, 2,3-dibromoselenophene, 2,3-dibromo-indole derivatives and 2-hydroxyphenylboronic acid derivatives as raw materials, The key intermediate 3 was obtained through the Suzuki reaction;

[0038] S102: Using cuprous or copper compounds (copper catalysts) as catalysts, 1,10-phenanthroline and other bipyridine compounds as ligands, 3 undergoes intramolecular Ullmann C-O coupling reaction, and synthesizes a series of fused ring furans Small molecule materials4.

[0039] The synthesis route of the preparation method based on the fused ring furan small molecule material provided by the embodiment of the present invention is as follows:

[0040]

[0041] Wherein Ar and Ar' are selected from any one of aryl, heteroaryl, aryl with subst...

Embodiment 1

[0059] Example 1 Benzo[4,5]thieno[3,2- b ] Synthesis of benzofuran

[0060]

[0061] 1) Accurately weigh 2,3-dibromobenzo[ b ]thiophene (683 mg, 2.34 mmol), 2-hydroxyphenylboronic acid (484 mg, 3.5mmol), and added to a 25 mL Schlenk bottle successively, potassium carbonate (1.29 g, 9.36 mmol), four (three Phenylphosphine) palladium (0.05 equivalent), 1,4-dioxane / water (volume ratio 4:1), placed in an oil bath at 90°C for 6 hours. After the reaction was over, the solvent was removed under reduced pressure, separated using a silica gel column, and petroleum ether / ethyl acetate was used as an eluent to obtain 2-(3-bromobenzo[ b ]thiophen-2-yl)phenol 3a in 84% yield. 1 H NMR (300 MHz, deuterated chloroform): δ 7.86-7.78 (m,2H), 7.47-7.32 (m, 4H), 7.04-6.98 (m, 2H), 5.35 (s, 1H). 13 C NMR (75 MHz, deuterated chloroform): δ 153.42, 138.82, 138.39, 133.55, 131.78, 131.29, 125.96, 125.52, 123.73, 122.45, 120.76, 119.09, 116.44, 108.63. Mass spectrum (EI mode): m / z C 1...

Embodiment 2

[0063] Example 2 Thieno[3,2- b ] Synthesis of benzofuran

[0064]

[0065] 1) Accurately weigh 2,3-dibromothiophene (504 mg, 2.1 mmol), 2-hydroxyphenylboronic acid (433 mg, 3.1 mmol), and add them to a 25 mL Schlenk bottle successively, and add potassium carbonate ( 828 mg, 6 mmol), tetrakis(triphenylphosphine) palladium (0.05 equivalent), 1,4-dioxane / water (volume ratio 4:1), placed in an oil bath at 90°C for 6 hours. After the reaction was over, the solvent was removed under reduced pressure, and the silica gel column was used for separation, and sherwood oil / ethyl acetate was used as eluent to obtain 2-(3-bromobenzene[ b ]thiophen-2-yl)phenol 3b in 87% yield. 1 H NMR (400 MHz, deuterated chloroform): δ 7.43 (d, J = 5.2 Hz, 1H),7.39-7.32 (m, 1H), 7.28 (dd, J = 8.8, 1.2 Hz, 1H), 7.12 (d, J = 5.6 Hz, 1H),7.01-6.98 (m, 2H), 5.13 (s, 1H). 13 C NMR (101 MHz, deuterated chloroform): δ 153.42, 133.16, 131.88, 131.04, 130.96, 127.37, 120.63, 118.80, 116.21, 111.05....

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Abstract

The invention belongs to the technical field of molecular materials and discloses a preparation method and application of a condensed ring furan-based small-molecular material. The method comprises the following steps: by taking 2,3-dibromofuran, 2,3-dibromothiophene, 2,3-dibromoselenophene, 2,3-dibromo-indol derivatives and 2-hydroxybenzeneboronic acid derivatives as raw materials, performing Suzuki reaction to obtain a key intermediate; by taking cuprous or a copper compound as a catalyst, and 1,10-phenanthroline or dipyridyl compound as a ligand, generating intramolecular Ullmann C-O coupling reaction, and synthesizing a series of condensed ring furan small-molecular materials. The substrate is relatively simple to synthesize and high in yield; the ring forming reaction time of furan is greatly shortened; the cuprous compound or dipyridyl compound as a catalyst system are cheap; the reaction conditions are milder; the application range of the substrate is wide; the reaction yield is high up to 97%. Therefore, the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of molecular materials, and in particular relates to a method for preparing a small molecule material based on condensed ring furan and its application. Background technique [0002] Organic semiconductor devices mainly include organic light emitting diodes (OLEDs), organic field effect transistors (OFETs) and organic solar cells (OPVs). Currently, OLEDs have been commercialized in some small devices, such as mobile phones, PDAs, digital cameras, and street lamps. However, OFETs and OPVs have made great progress in practical application and are moving towards industrialization. One of the important ways to improve the properties of organic semiconductor devices is to develop new organic molecular materials. Organic molecular materials are a class of organic optoelectronic materials that contain π-electron structures and have optical, electrical, and magnetic properties, also known as organic semiconductor ...

Claims

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Application Information

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IPC IPC(8): C07D495/04C07D495/22C07D493/04H01L51/54
CPCC07D493/04C07D495/04C07D495/22H10K85/657H10K85/6574H10K50/00
Inventor 李保林陈道良
Owner UNIVERSITY OF CHINESE ACADEMY OF SCIENCES
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