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Preparation method for tin-fluorene compound

A compound, tin fluorene technology, applied in the field of organic semiconductor material preparation, can solve the problems of harsh reaction conditions, poor reproducibility, difficult reaction operation, etc., and achieve the effect of realizing reaction conditions, simple operation, and easy reaction conditions.

Active Publication Date: 2019-02-26
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In order to solve the problems of harsh reaction conditions, difficult reaction operation and poor reproducibility in the current method for synthesizing tinfluorene compounds, the present invention proposes a preparation method of tinfluorene compounds, the reaction conditions are easy to realize, and the operation is simple , purification steps, cost reduction, and the synthesis of tin fluorene compounds can be used as reactants to continue to react to become chain or cyclic macromolecular compounds

Method used

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  • Preparation method for tin-fluorene compound
  • Preparation method for tin-fluorene compound
  • Preparation method for tin-fluorene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Add 4.24g (10mmol) of 3,3'-dibromo-2,2'-dibenzothiophene, 11.9g (0.1mol) of tin powder, and 25.2mg of iodine into a 250ml single-necked flask equipped with a mechanical stirring device and a reflux device (0.1mmol), organic solvent xylene 100ml. Heated to reflux at 160°C for 12h. The reaction was monitored by thin-layer chromatography. After the reaction, the solvent was evaporated in vacuo, and dichloromethane was added to dissolve and then extracted. After the extraction, the organic phase was dried with anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the crude product was separated by column chromatography to obtain 4.88 g of product 1 with a yield of 90%. The structural formula of product 1 is as follows:

[0028]

Embodiment 2

[0030] Add 5.18g (10mmol) of 3,3'-diiodo-2,2'-dibenzothiophene, 2.38g (20mmol) of tin powder, 127mg (0.5 mmol), organic solvent toluene 100ml. Heat to reflux at 120°C for 15h. Thin-layer chromatography monitors and reflects that after the reaction is completed, the solvent is evaporated in vacuo, and dichloromethane is added to dissolve and then extracted. After extraction, the organic phase is dried with anhydrous magnesium sulfate. After extraction, the organic phase was dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the crude product was separated by column chromatography to obtain 5.60 g of product 2 with a yield of 88%. The structural formula of product 2 is as follows:

[0031]

Embodiment 3

[0033] Add 4.68g (10mmol) of 3,3'-dibromo-[2,2'-dithiophene]-5,5'-bistrimethylsilane to a 250ml single-necked flask equipped with a mechanical stirring device and a reflux device, tin Powder 5.95g (50mmol), iodine 101.4mg (0.4mmol), organic solvent benzene 100ml. Heated to reflux at 100°C for 14h. Thin-layer chromatography monitors and reflects that after the reaction is completed, the solvent is evaporated in vacuo, and dichloromethane is added to dissolve and then extracted. After extraction, the organic phase is dried with anhydrous magnesium sulfate. After extraction, the organic phase was dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the crude product was separated by column chromatography to obtain 5.37 g of product 3 with a yield of 92%. The structural formula of product 3 is as follows:

[0034]

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Abstract

The invention provides a preparation method for a tin-fluorene compound to overcome the problems of demanding reaction conditions, difficult reaction operation, poor reproducibility and the like of conventional synthesis methods for tin-fluorene compounds, belonging to the field of preparation of organic semiconductor materials. The preparation method comprises the following steps: under the protection of inert gas, adding dihaloalkane, tin powder, a catalyst and an organic solvent into a reactor, and carrying out a reaction at 100-160 DEG C for 12-15 h; then carrying out cooling to room temperature; successively performing extraction, collecting an organic phase and carrying out drying to obtain a coarse product; and treating the coarse product to obtain the tin-fluorene compound. The preparation method of the invention has the advantages of easily-implementable reaction conditions, simple operation, implementation of a purification step and reduced cost; and the synthesized tin-fluorene compound can be used as a reactant for a subsequent reaction so as to form a chain-like or cyclic macromolecular compound.

Description

technical field [0001] The invention relates to the field of preparation of organic semiconductor materials, in particular to a new method for preparing tinfluorene (like compounds). Background technique [0002] In recent years, many research institutions at home and abroad have developed a large number of organic small molecules and polymer materials with novel structures, and have been applied to organic field effect transistors (OFETs), semiconductor gas sensors, thermal linear sensors, non-conductive FET field Effect transistors, gas sensors, solar cells and other organic electronic devices have greatly promoted the development of the field of organic semiconductors. Among the organic semiconductor materials reported in the literature, dithienotinfluorene (DTSn) materials are an important class of organic donor materials. The group IVA element tin is introduced as a bridging atom into the thiophene conjugated main chain to form a σ* The -π* conjugated structure can eff...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/22
Inventor 张飞豹高占臣吕素芳蒋剑雄
Owner HANGZHOU NORMAL UNIVERSITY