Novel polymerization method of conjugated polymer based on (2-oxyindole-3-idene) benzodifuran-dione and bithiophene

A benzodifuran and conjugated polymer technology, which is applied in the field of organic polymer preparation, can solve the problems of high reaction conditions, toxic and expensive catalysts, etc., and achieves low reaction cost, high atom utilization, and efficient preparation. Effect

Inactive Publication Date: 2016-09-21
HEFEI UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the method for preparing this type of organic semiconducting polymer is mainly through the Stille polymerization method, but this traditional polymerization method has problems such as the toxicity of tin monomer, the toxicity and high cost of the catalyst, and the high requirements for reaction conditions. The present invention designs an aldol based A Novel Polymerization Method for the Preparation of Conjugated Semiconducting Polymers of (2-oxindol-3-ylidene)benzodifuran-dione and Dithiophene by Condensation Reaction

Method used

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  • Novel polymerization method of conjugated polymer based on (2-oxyindole-3-idene) benzodifuran-dione and bithiophene
  • Novel polymerization method of conjugated polymer based on (2-oxyindole-3-idene) benzodifuran-dione and bithiophene
  • Novel polymerization method of conjugated polymer based on (2-oxyindole-3-idene) benzodifuran-dione and bithiophene

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preparation example Construction

[0018] The preparation method of each monomer is described as follows:

[0019] The specific steps for the synthesis of monomer 1 thiophene dibenzopyrrole diketone: hexabromoisatin and thiophene boron monomers can be purchased directly, and hexabromoisatin and potassium carbonate react with brominated alkyl chains in DMF The obtained compound is then reacted with thiophene boron monomer to obtain monomer 1 through conventional Suzuki cross-coupling reaction. The synthetic route is shown as follows:

[0020]

[0021] Synthetic steps for preparing monomer 2 benzodifurandione: benzodifurandione monomer is prepared by literature method, detailed preparation method can be found in literature report (Journal of the American Chemical Society, 135(33), 12168-12171 ; 2013), the synthetic route of monomer benzodifurandione is shown as follows:

[0022]

Embodiment 1

[0023] Embodiment 1, synthetic polymer P1

[0024] The specific steps for the synthesis of polymer P1 are as follows: add 0.180g (0.123mmol) of monomer 1 and 0.023g (0.123mmol) of monomer 2 into a 100mL polymerization reaction tube, and then add 0.06g (0.315mmol) of toluenesulfonic acid as a catalyst, After dissolving the above substances with 5mL of toluene, use N 2 The air was exhausted for 15 minutes, and the reaction was sealed at 120°C for 48 hours. Cool the reaction to room temperature, add 200mL of methanol to precipitate, filter the solid, extract with methanol and n-hexane Soxhlet for 24 hours, and then use chloroform for 24 hours, and finally rotate the liquid, and precipitate with methanol to obtain a polymer, polymer P1 The synthesis path is shown as follows:

[0025]

Embodiment 2-3

[0027] The specific steps are the same as in Example 1: add 0.123mmol monomer 1 and 0.123mmol monomer 2 in the 100mL polymerization reaction tube, then add catalyst 0.315mmol toluenesulfonic acid (catalyst amount can be changed correspondingly according to solvent amount and reaction time), use After dissolving the above substances in 5mL toluene, use N 2 The air was exhausted for 15 minutes, and the reaction was sealed at 120°C for 48 hours. Cool the reaction to room temperature, add 200mL of methanol to precipitate, filter the solid, extract with methanol and n-hexane Soxhlet for 24 hours, and then extract with chloroform for 24 hours, finally spin the liquid, and precipitate with methanol to obtain polymers P2-P3. The specific structure is shown in Table 1.

[0028] Table 1

[0029]

[0030] In summary, the present invention relates to a novel polymerization method based on a conjugated polymer of (2-oxindol-3-ylidene)benzodifuran-dione and thiophene. The D-A type con...

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Abstract

The invention discloses a novel polymerization method of a conjugated polymer based on (2-oxyindole-3-idene) benzodifuran-dione and bithiophene. According to the novel active polymerization method, a polymerization reaction is carried out by taking bithiophene dibenzodipyrrole dione and benzodifuran dione as basic compounds and taking acid as a catalyst in a solvent, such as chlorobenzene or methylbenzene, and thus the polymer can be efficiently prepared. The polymerization method is novel in design and easy in activity control, is efficient, and can be applied to preparation of semiconductor polymers of such type. The polymer has a structural formula shown in the description. In the formula, R1 is a C8-C24 alkyl chain, R2 is H or a C6-C14 alkyl chain, and n is no less than 1.

Description

technical field [0001] The invention relates to the field of organic polymer preparation, in particular to a novel polymerization method of a conjugated semiconducting polymer based on (2-oxindole-3-ylidene) benzodifuran-dione and thiophene. Background technique [0002] In recent years, research on the application of donor / acceptor (D / A) conjugated polymers in organic thin film transistors (OTFT) and organic photovoltaics (OPV) has gradually attracted people's attention. It has been reported in the literature that bis(6-bromo-1-(2-decyltetradecyl) 2-oxindole 3-ylidene) benzodifuran-dione (BIBDF) is a derivative of isoindigo (Benzodifurandione is introduced into the isoindigo structure), which has large fused aromatic rings and a symmetrical two-dimensional planar structure, which can increase π-π stacking and intermolecular forces. The lactone group and lactam group in the center of the BIBDF structure make it have a strong electron-withdrawing ability. If BIBDF groups ar...

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Application Information

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IPC IPC(8): C08G61/12
CPCC08G61/124C08G61/125C08G61/126C08G2261/12C08G2261/1412C08G2261/18C08G2261/3241C08G2261/3242C08G2261/91C08G2261/92
Inventor 张国兵刘家庆郭景华吕国强
Owner HEFEI UNIV OF TECH
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