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Asymmetric thiophene [7] helicene isomer as well as preparation method and application thereof

An isomer and asymmetric technology, applied in the field of helicene compounds, can solve problems such as unreported research work, achieve high yield, less by-products, and improved performance

Active Publication Date: 2020-04-24
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] However, the reported thiophene[7]helicenes are all symmetrical structures. Due to the isomerization of S atoms in the molecule and the isomerization of the molecular skeleton, there are many isomers of thiophene[7]helicenes, but they are asymmetrical. There are great challenges in the synthesis of thiophene[7]helicene, and related research work has not been reported

Method used

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  • Asymmetric thiophene [7] helicene isomer as well as preparation method and application thereof
  • Asymmetric thiophene [7] helicene isomer as well as preparation method and application thereof
  • Asymmetric thiophene [7] helicene isomer as well as preparation method and application thereof

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Embodiment 1

[0043] This embodiment provides a preparation method of thiophene [7] helicene TM-1, comprising the following steps:

[0044] (1) Preparation of Compound 2, the reaction equation is as follows:

[0045]

[0046] The specific method is: add compound 1 (179.6mg, 0.52mmol, 1.0eq) into a dry 50mL long Schlenk bottle, dry in vacuum for about 0.5h, add 25mL of anhydrous ether to dissolve under the protection of argon, cool to -78°C, Add t-BuLi (0.92mL, 1.2M in pentane, 1.06mmol, 2.05eq) dropwise, react at -70°C for 2h; add isopropanol pinacol borate (0.11mL, 0.54mmol , 1.05eq), naturally warmed to room temperature and stirred overnight; -78°C, methanol was added to quench the reaction, the solvent was removed, the aqueous phase was extracted with dichloromethane (3×10mL), the combined organic phase was washed with water (2×20mL) The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed, separated and purified by column chromatography (el...

Embodiment 2

[0055] This embodiment provides a preparation method of thiophene [7] helicene TM-2, comprising the following steps:

[0056] (1) Preparation of Compound 2, the reaction equation is as follows:

[0057]

[0058] The specific method is: add compound 1 (179.5mg, 0.52mmol, 1.0eq) into a dry 50mL long Schlenk bottle, dry it in vacuum for about 0.5h, add 25mL anhydrous ether to dissolve under the protection of argon, cool to -70°C, Add n-BuLi (1.12mL, 1.46M in pentane, 1.29mmol, 2.5eq) dropwise, and react at -70°C for 1h; ), naturally rose to room temperature and stirred overnight; - 70 ° C, methanol was added to quench the reaction, the solvent was removed, the aqueous phase was extracted with dichloromethane (3 × 10 mL), the organic phase was combined, and the organic phase was washed with water (2 × 20 mL). Dry over anhydrous magnesium sulfate, filter, remove the solvent, separate and purify by column chromatography (eluent: petroleum ether first, then ethyl acetate) to obta...

Embodiment 3

[0067] This embodiment provides a preparation method of thiophene [7] helicene TM-3, comprising the following steps:

[0068] (1) The preparation of compound 8, the reaction equation is as follows:

[0069]

[0070] The specific method is: add compound 7 (179.6mg, 0.52mmol, 1.0eq) into a dry 50mL long Schlenk bottle, dry it in vacuum for about 0.5h, add 25mL anhydrous ether to dissolve under the protection of argon, cool to -90°C, Add t-BuLi (0.98mL, 1.29M in pentane, 1.14mmol, 2.2eq) dropwise, react at -70°C for 3h; add isopropanol pinacol borate (0.13mL, 0.62mmol , 1.2eq), naturally warmed to room temperature and stirred overnight; Added methanol to quench the reaction at -90°C, removed the solvent, extracted the aqueous phase with dichloromethane (3×10mL), combined the organic phases, and washed with water (2×20mL) The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed, separated and purified by column chromatography (eluent:...

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Abstract

The invention relates to an asymmetric thiophene [7] helicene isomer as well as a preparation method and application thereof. The preparation method comprises the following steps: preparing an asymmetric dithienothiophene dimer compound through a coupling reaction, carrying out LDA deprotonation on the asymmetric dithienothiophene dimer compound, and carrying out (PhSO2)2S thiocyclization to prepare the double-TMS substituted asymmetric thiophene [7] helicene isomer. The brand-new asymmetric thiophene [7] helicene isomer has an excellent performance, is particularly suitable for being used asan organic semiconductor material, and is applied to organic light emitting diodes, organic field effect transistors and organic solar cells.

Description

technical field [0001] The application belongs to the technical field of helicene compounds, and in particular relates to an asymmetric thiophene [7] helicene isomer and its preparation method and application. Background technique [0002] Helicene compounds are polycyclic aromatic compounds with a helical structure formed by the ortho-condensation of aromatic rings. At present, helicene compounds have good applications in the fields of asymmetric catalysis, molecular recognition, fluorescence sensing, and chiral optical materials. Helicenes are divided into carbohelicenes and heterohelicenes. Thiophene helicenes are an important part of heterohelicenes. The reported thiophene helicenes include thiophene[5]heliene, thiophene[7]heliene, thiophene[9] The preparation of helicene, thiophene[11]helicene, and thiophene[7]helicene is a pioneering work, and its typical preparation methods are shown in the following two reaction formulas. [0003] [0004] Synthesis of Thiophene[...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08H01L51/30H01L51/46H01L51/54
CPCC07F7/0814C07F7/083H10K85/6576Y02E10/549
Inventor 王华王金健王光霞李春丽史建武
Owner HENAN UNIVERSITY
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