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Asymmetric seven-membered fused thiophene as well as preparation method and application thereof

A fused thiophene, asymmetric technology, applied in the field of preparation of organic compounds, can solve the problems of affecting the intermolecular stacking mode, affecting the optoelectronic properties of materials, etc., and achieve the effect of high yield and excellent performance

Active Publication Date: 2018-11-23
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the positional isomerism and molecular skeleton isomerization of the S atom in the heptathiophene structure, there are many isomers, and these isomers can exhibit various intermolecular forces, and the existence of these forces may Affects the stacking mode between molecules, which in turn affects the photoelectric properties of the material

Method used

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  • Asymmetric seven-membered fused thiophene as well as preparation method and application thereof
  • Asymmetric seven-membered fused thiophene as well as preparation method and application thereof
  • Asymmetric seven-membered fused thiophene as well as preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0049] This embodiment provides a preparation method of asymmetric heptathiophene substituted with double TMS, including the following steps:

[0050] (1) Preparation of 6-trimethylsilyl-3-pinacol ester-dithieno[2,3-b:2',3'-d]thiophene (3), the reaction equation is as follows:

[0051]

[0052] The specific method is: add compound 2 (679mg, 1.95mmol) to dry 100mL Schlenk, vacuum dry for 0.5h, add 50mL anhydrous ether under the protection of argon, stir well to dissolve, then transfer to -78℃ cryostat Keep stirring under argon for 10min; slowly add t-BuLi (1.28M in Pentane, 3.2mL, 4.10mmol, 2.1eq), react at -78℃ for 2h; add isopropanol pinacol borate (0.47mL , 2.34mmol, 1.2eq), slowly warm to room temperature, and stir for 10h. Add 2mL CH 3 OH quenched the reaction, removed the solvent, and added 30 mL saturated NaHCO 3 Solution, use 4×15mL CH 2 Cl 2 Extract the aqueous phase, combine the organic phases, and use 3×15mL H 2 O wash the organic phase, anhydrous MgSO 4 Fully dry, filte...

Embodiment 2

[0062] This embodiment provides a preparation method of asymmetric heptathiophene substituted with double TMS, including the following steps:

[0063] (1) Preparation of 6-trimethylsilyl-3-pinacol ester-dithieno[2,3-b:2',3'-d]thiophene (3), the reaction equation is as follows:

[0064]

[0065] The specific method is: add compound 2 (678mg, 1.95mmol) to dry 100mL Schlenk, vacuum dry for 0.5h, add 50mL anhydrous ether under the protection of argon, stir well to dissolve, then transfer to -70℃ cryostat Keep stirring for 10min; slowly add n-BuLi (1.28M in Pentane, 3.81mL, 4.88mmol, 2.5eq), and react at -70℃ for 2h; add pinacol diboronate (0.39mL, 1.95mmol) under argon protection , 1eq), slowly warm to room temperature, and stir for 8h. Add 2mLCH 3 OH quenched the reaction, removed the solvent, and added 30 mL saturated NaHCO 3 Solution, use 4×15mL CH 2 Cl 2 Extract the aqueous phase, combine the organic phases, and use 3×15mL H 2 O wash the organic phase, anhydrous MgSO 4 Fully dry, ...

Embodiment 3

[0073] This embodiment provides a preparation method of asymmetric heptathiophene substituted with double TMS, which includes the following steps:

[0074] (1) Preparation of 6-trimethylsilyl-3-pinacol ester-dithieno[2,3-b:2',3'-d]thiophene (3), the reaction equation is as follows:

[0075]

[0076] The specific method is: add compound 2 (679mg, 1.95mmol) to dry 100mL Schlenk, vacuum dry for 0.5h, add 50mL anhydrous ether under the protection of argon, stir well to dissolve, then transfer to -90℃ cryostat Keep stirring in medium for 20min; slowly add t-BuLi(1.28M in Pentane, 3.2mL, 4.10mmol, 2.1eq), react at -90℃ for 5h; add isopropanol pinacol borate (0.59mL , 2.93mmol, 1.5eq), slowly rise to room temperature, and stir for 14h. Add 2mL CH 3 OH quenched the reaction, removed the solvent, and added 30 mL saturated NaHCO 3 Solution, use 4×15mL CH 2 Cl 2 Extract the aqueous phase, combine the organic phases, and use 3×15mL H 2 O wash the organic phase, anhydrous MgSO 4 Fully dry, fil...

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Abstract

The invention relates to asymmetric seven-membered fused thiophene as well as a preparation method and application thereof. The preparation method comprises the following steps: S1, enabling 3-bromo-6-trimethylsilyl-dithieno [2, 3-b: 2', 3'-d] thiophene to be first exchanged with lithium alkyl bromide, and then adding pinacol borate for carrying out a reaction so as to prepare 6-trimethylsilyl-3-pinacol ester-dithieno [2, 3-b: 2', 3'-d] thiophene; S2, enabling the product, obtained in the S1, and 5-bromo-2-trimethylsilyl-dithieno [3, 2-b: 2', 3'-d] thiophene to be subjected to Suzuki couplingto prepare 2-trimethylsilyl-5-(6-trimethylsilyl-dithieno [2, 3-b: 2', 3'-d] thiophene-3) dithieno [3, 2-b: 2', 3'-d] thiophene; S3, enabling the product, obtained in the S2, to be subjected to deprotonation by means of LDA and subjected to (PhSO2) 2S thio ring closing so as to prepare the asymmetric seven-membered fused thiophene. The asymmetric seven-membered fused thiophene can be applied in oganic light emitting diodes, organic field effect transistors and organic solar cells as an organic semiconductor material.

Description

Technical field [0001] The invention relates to an asymmetric seven-membered fused thiophene and a preparation method and application thereof, and belongs to the technical field of organic compound preparation. Background technique [0002] Condensed thiophene compounds are a class of thiophene oligomers formed by the fusion of thiophene units through aromatic rings. Currently, fused thiophene compounds as organic semiconductor materials have been applied to organic light-emitting diodes, organic field effect transistors and organic solar cells. Oligothiophenes synthesized based on tetrathiophene (tetrathiophene and pentathiophene and its derivatives) have shown attractive application prospects in the field of organic optoelectronics. As a type of typical condensed thiophene oligomers, heptathiophene has various molecular configurations, such as spiral, horn, and linear. Compared with pentathiophene and pentathiophene, the conjugated system of heptathiophene is larger, and it i...

Claims

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Application Information

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IPC IPC(8): C07D495/22C07F7/08C09K11/06H01L51/05H01L51/30H01L51/50H01L51/54
CPCC09K11/06C07D495/22C07F7/0814C07F7/083C09K2211/1092H10K85/6576H10K85/40H10K10/46H10K50/11Y02E10/549
Inventor 王华李春丽张超史建武宋金生王光霞
Owner HENAN UNIVERSITY
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