Bithienofluorene, its derivative and preparation method

A technology for bis-thieno-fluorene derivatives, applied in the field of bis-thieno-fluorene derivatives and their preparation

Inactive Publication Date: 2013-06-12
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, there is no report on the introduction of fluorene into bisthiophene ring compounds

Method used

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  • Bithienofluorene, its derivative and preparation method
  • Bithienofluorene, its derivative and preparation method
  • Bithienofluorene, its derivative and preparation method

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Embodiment Construction

[0046] See attached figure 1 , the invention discloses a bisthienofluorene and its derivatives, which are characterized in that fluorene is connected to two thiophene groups in parallel rings, and there is a substituent at the 2-position of thiophene, and sodium sulfide is not only used as the sulfur element of the thiophene ring Source and as a reducing agent for fluorenone carbonyl reduction; its preparation is carried out in the following steps:

[0047] Preparation of 3,6-dichloro-2,7-dihydroxy-9-fluorenone (a)

[0048] Under nitrogen protection, 2,7-dihydroxyfluorenone (10.490 g, 49.5 mmol) was dissolved in 250 mL of glacial acetic acid to form a suspension, stirred, and slowly heated to 42 °C. Sulfonyl chloride (20 mL, 247.4 mmol) was slowly added dropwise, keeping the temperature below 45 °C. The suspension gradually changed from dark red to orange. React for 40 minutes after dropping. Cool, filter with suction, and wash with water and acetone. An orange sol...

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Abstract

The invention discloses bithienofluorene, its derivative and a preparation method. The compounds are characterized in that: a fluorene ring is in connection with thieno rings, and the 2- position of thiophene has a substituent group, which can be hydrogen, alkyl or aryl. The preparation method consists of: taking 2, 7-dyhydroxyl-9-fluorenone as a raw material, employing sulfonyl chloride to conduct chlorination so as to synthesize 3, 6-dichloro-2, 7-dyhydroxyl-9-fluorenone; and then adopting trifluoromethanesulfonic anhydride to carry out esterification, and performing a Sonogashira coupling reaction to obtain series of 2, 7-disubstituted ethynyl-3, 6-dichloro-9-fluorenone, and finally conducting ring closing by sodium sulfide and reduction to obtain bithienofluorene and its derivative. The series of compounds involved in the invention provides a new option for organic field effect transistor materials, and the preparation method provides a new method for aromatic ketone carbonyl reduction.

Description

Technical field [0001] The present invention is an organic semiconductor material field. Specifically, it is a type of double pneumophyte and derivatives and preparation methods and applications. Background technique [0002] The airport effects crystal has the characteristics of wide material sources, simple preparation process, low cost, and suitable for large production, and can be compatible with flexible substrates. This is unmatched by the airport effect crystal.In recent years, it has received more and more attention and has become a hot spot in the field of organic optical electronic function materials and device research.It can be widely used in many fields such as all organic and active display, large -scale and ultra -large -scale integrated circuits, complementary logic circuits, memory components, sensors, organic laser and superconducting materials. [0003] Among the many airport effects of crystalline tube materials, five benzene is one of the most promising mater...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04
Inventor 刘乾才熊小丽
Owner EAST CHINA NORMAL UNIV
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