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Position fixable polymerized precursor of polythiazole monomer and its synthesis

A synthesis method and technology of polythiophene are applied in the field of preparing precursors of thiophene polymer monomers, which can solve the problems of long reaction period, low yield of final product compounds, and difficulty in obtaining ideal yields, and shorten the reaction time. Effect

Inactive Publication Date: 2005-07-27
徐良衡
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, for a long time, the alkylation of corresponding esters or corresponding alkali metal and alkaline earth metal phenates has been difficult to obtain an ideal yield or the process is too complicated, which makes it difficult to achieve industrial transformation
The synthesis process of 3,4-alkoxythiophene dicarboxylic acid is complex and difficult to synthesize. The most important thing is that the yield of the final product compound is not high and the reaction cycle is long

Method used

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  • Position fixable polymerized precursor of polythiazole monomer and its synthesis
  • Position fixable polymerized precursor of polythiazole monomer and its synthesis
  • Position fixable polymerized precursor of polythiazole monomer and its synthesis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Add 5.0 g (0.028 mol) of dimethyl thiodiglycolate, 8 g (0.055 mol) of diethyl oxalate, and 1.5 g of potassium carbonate into reactor 1 containing 50 ml of anhydrous methanol, and mix well. Mix 7.5g (0.14mol) of sodium methoxide with 65ml of anhydrous methanol and pour it into a three-neck flask 2 with block anhydrous copper sulfate built in, cool down to make the reaction solution 0-2°C, and put the The ester mixture was slowly added dropwise into flask 2, and after the dropwise addition was completed, it was heated to reflux for a reaction time of 1.5 hours. Suction filtration, repeated (3-5 times) washing with anhydrous methanol, vacuum drying to obtain the reaction product 2,5-dicarboxylate-3,4-diphenol sodium thiophene 6.95g, yield 90%, HPLC : 92.0%.

[0053] Elemental analysis value of the product: C, 35.3%; H, 2.40%.

[0054] Infrared Spectrum Absorption Peak: The absorption peak is 1725cm -1 , The absorption peak is 1532cm -1 , 2955cm -1 It is the absorp...

Embodiment 2

[0057] 6.4g (0.031mol) diethyl thiodiglycolate, and 15 grams (0.103mol) diethyl oxalate, 1.6g potassium carbonate were added together in the glass reaction bottle a that 50ml absolute ethanol was housed, and 20g ( 0.082mol) of sodium trityl was mixed with 20ml of ethanol and then added to another reaction bottle b with a built-in desiccant of block CaO, and the temperature was controlled at -2°C-0°C. Slowly add the ester mixture into the reaction bottle a dropwise. After the dropwise addition, the temperature is raised to 80° C., and the reaction time is 1.5-2.0 h. After suction filtration, washing with water three times, and vacuum drying, 7.4 g of the product 2,5-dicarboxylate-3,4-diolthiophene was obtained, with a yield of 89%. HPLC: 93.0% purity.

[0058] Elemental analysis results: C, 46.1%; H, 4.7%; O, 37.0%; S, 12.4%

[0059] The infrared spectrum analysis result of product is as follows:

[0060] The absorption peak is 1728cm -1 , the absorption peak of the carbo...

Embodiment 3

[0068] Embodiment 3 (mixed solvent)

[0069] 8.0g of diethyl thiodiglycolate, together with 15 grams (0.103mol) of diethyl oxalate, and 2.0g of sodium carbonate were added to a glass reaction bottle a containing 50ml of anhydrous methanol, and 20g of sodium ethylate was mixed with 75ml of After mixing absolute ethanol, add it to the built-in block anhydrous CaSO 4In another reaction bottle b of the desiccant, the temperature is controlled at 0°C-2°C. Slowly add the ester mixture into the reaction flask b dropwise. After the dropwise addition, the temperature is raised to 70° C., and the reaction time is 2.5-3.0 h. After suction filtration, washing with water three times, and vacuum drying, the product 2,5-ethyl dicarboxylate-3,4-diolthiophene was obtained with a yield of 88.5%. HPLC: 93.5%.

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Abstract

A 3,4-alkdioxthipphene and 3,4-alkylenedioxthipphene-2,5-dicarboxylic acid ester and its synthesizing method are disclosed. The method is carried out by: taking thiodiglycol diester as materials, comprehensive reacting with Arrcostab oxalate, obtaining intermediate product, and alkylation reacting. It achieves simple operation, and short reacting period.

Description

technical field [0001] The invention belongs to the field of fine chemical organic synthesis, and relates to a synthesis method of dioxythiophene derivatives, in particular to a synthesis method of 3,4-substituted thiophene dicarboxylic acids, especially 3,4-alkyldioxy A method for synthesizing two types of compounds of thiophene and 3,4-alkylene dioxythiophene-2,5-dicarboxylic acid. In addition, the compounds involved in the present invention are precursors for preparing thiophene polymer monomers. technical background [0002] Since the 1970s, the synthesis and development of thiophene derivatives have been widely concerned by the academic community. Especially after the formation of the new branch of material science, conductive polymers, conductive thiophene and its derivatives have attracted much attention from academia and industry due to their attractive application prospects in modern optoelectronics, microelectronics, and modern medicine. In order to clarify the r...

Claims

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Application Information

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IPC IPC(8): C07D333/40C08G75/00
Inventor 徐良衡王群英李想高芸
Owner 徐良衡
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