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Preparation of 2,2'-di(3,4-ethylenedioxy-thiophene)

A C6-C14, alkyl technology, applied in the field of preparation 2, can solve the problems of increased reaction time, air and moisture sensitivity, no mention of having alkylene bridges, etc.

Inactive Publication Date: 2009-07-01
HERAEUS PRECIOUS METALS GMBH & CO KG
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But for this, the reaction time must be increased by a factor of 6
[0011] Significant disadvantages of the 2,2'-bis(3,4-ethylenedioxythiophene) preparation methods used in all these publications are: 1) For the lithiation, an external cooling mixture such as acetone / dry ice has to be used, Make it at low temperature (-78°C)
2) As an organometallic reagent, n-butyllithium is expensive and sensitive to air and moisture during operation, especially flammable when moisture enters
2,2'-bis(3,4-alkylenedioxythiophene) with an alkylene bridge instead of an ethylene bridge has also not been mentioned so far in the literature

Method used

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  • Preparation of 2,2'-di(3,4-ethylenedioxy-thiophene)
  • Preparation of 2,2'-di(3,4-ethylenedioxy-thiophene)
  • Preparation of 2,2'-di(3,4-ethylenedioxy-thiophene)

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Experimental program
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Effect test

Embodiment 1

[0105] Embodiment 1: prepare 2,2'-two (3,4-ethylenedioxythiophene) (I-a) (the present invention)

[0106]

[0107] 28.64 g (0.1 mol) of EDT dimer (II-a) were dissolved in 500 ml of xylene. To this solution was added 24.59 g (0.1 mol) of chloranil. The mixture was heated to reflux at 140°C for 10 hours. After cooling, the precipitated crystals were filtered off with suction, and the crystals and the mother liquor were worked up further.

[0108] The mother liquor was washed 4 times with 50 ml of 4% potassium hydroxide solution each time, and finally washed with water until neutral. The solution was concentrated by evaporation and dried under high vacuum, yielding 15.8 g of crude product as green crystals (fraction A).

[0109] The suction-filtered crystals were slurried with 150 ml of xylene and 100 ml of 4% strength potassium hydroxide solution, and the insoluble fraction (5.5 g) was removed by filtration. The mother liquor was worked up in the same manner as above, a...

Embodiment 2

[0114] Embodiment 2: prepare 2,2'-bis(3,4-ethylenedioxy with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone base thiophene) (I-a)

[0115] 8.53 g (30 mmol) of EDT dimer (II-a) were dissolved in 150 ml of xylene. To this solution was added 7.15 g (31.5 mmol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. The mixture was heated to reflux at 140°C for 24 hours. After cooling, the mixture was extracted with 4% potassium hydroxide solution until the potassium hydroxide solution remained colorless. Finally the mixture was washed with water until neutral. The solution was concentrated by evaporation and dried under high vacuum, yielding 3.68 g (43.5% of theory) of crude product as a beige residue. The crude product was purified by column chromatography on silica gel eluting with dichloromethane.

[0116] 1.32 g (15.6% of theory) of pure 2,2'-bis(3,4-ethylenedioxythiophene) (I-a) were isolated. Melting point: 207-209°C.

[0117] 1 H NMR spectrum (400MHz, CDCl 3 ) is the same as ...

Embodiment 3

[0118] Example 3: Preparation of dimethyl-2,2-3,3'-tetrahydro-5,5'-dithieno[3,4-b]1,4-dioxin (II-b)

[0119]

[0120] 0.85 g (2.7 mmol) of methyl-EDT dimer (II-b) was dissolved in 50 ml of xylene. To this solution was added 0.668 g (2.7 mmol) of chloranil. The mixture was heated to reflux at 140°C for 14 hours. After cooling, the mixture was diluted with dichloromethane and extracted with 4% potassium hydroxide solution until the potassium hydroxide solution remained colorless. Finally, the mixture is washed with water until neutral. The solution was concentrated by evaporation and dried under high vacuum, yielding 0.48 g (56.7% of theory) of crude product (I-b) as residue. The product was purified by column chromatography on silica gel eluting with dichloromethane. Pure yield 0.38 g (44.8% of theory).

[0121] 1 H NMR spectrum (400MHz, CDCl 3 , ppm): 6.24, 6.235, 6.23 (3s, 2H), 4.39 (with more split q, 3 J=6.56Hz) and 4.32 (q with more splits, 3 J=6.56Hz, all ar...

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Abstract

Preparing a neutral or a cationic compound (I), comprises polymerizing a thiophene compound (II) by chemical or electrochemical oxidation. The (I) is cationic and carries a maximum of m+2 positive charge. Preparing a neutral or a cationic compound of formula (I), comprises polymerizing a thiophene compound of formula (II) by chemical or electrochemical oxidation. The (I) is cationic and carries a maximum of m+2 positive charge. A : 2-4C alkylene; R : optionally branched, optionally substituted 1-18C alkyl, optionally substituted 5-12C cycloalkyl, optionally substituted 6-14C aryl, optionally substituted 1-4C hydroxyalkyl or OH; x : 0-8; and m : 2-100. [Image].

Description

technical field [0001] The present invention relates to the preparation of 2,2'-bis(alkylenedioxythiophene) (also known in literature as 2,2'-bis(3,4-alkylenedioxythiophene) or 3,4-(alkylenedioxythiophene) Alkanedioxy)-2,2'-thiophene), as well as novel compounds of this class of substances, and their use as important precursors or for the preparation of π-conjugated polymers. Background technique [0002] In recent decades, numerous publications have been the subject of such π-conjugated polymers. They are also known as conductive polymers or synthetic metals. [0003] Due to the significant delocalization of π-electrons along the backbone, these polymers exhibit interesting (nonlinear) optical properties, and after oxidation or reduction, they are good electrical conductors. This makes these compounds useful in many practical applications, such as in data storage, optical signal processing, suppression of electromagnetic interference (EMI), and solar energy conversion, bu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/00C07D497/00C07D409/04C07D495/04C08G61/12H01L51/05H01L51/30H01L51/40
CPCC08G61/123C08G61/126C07D495/04
Inventor K·鲁特
Owner HERAEUS PRECIOUS METALS GMBH & CO KG
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