Star-shaped oligothiophene derivative, preparation method and application thereof

A technology of thiophene derivatives and thiophene groups is applied in the field of star-shaped oligomerized thiophene derivatives and their preparation, which can solve the problems of unsuitable flexible processing, high manufacturing cost, difficult film formation, etc. Effects of film formation, oxidation state and reduction state stabilization

Active Publication Date: 2013-10-30
珠海尚明光电有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, almost all electrochromic materials are inorganic transition metal oxides. The manufacturing cost of inorganic electrochromic materials is high, it is not easy to form a film, and it is not suitable for flexible processing. Moreover, some inorganic transition metal oxides also have non-degradable toxicity.

Method used

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  • Star-shaped oligothiophene derivative, preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 1) Preparation of 3TB-2CHO:

[0043] In the first step, under the protection of nitrogen, add N , N -Dimethylformamide, slowly dropwise adding phosphorus oxychloride, controlling the reaction temperature to 30°C, stirring and reacting for 65 minutes to obtain a reaction solution;

[0044] In the second step, 1,3,5-tri(2 ' -thienyl)-benzene, stirred and reacted for 35 minutes to obtain a reaction solution;

[0045] In the third step, after the reaction is over, add distilled water to the reaction solution obtained in the second step for hydrolysis, and the obtained flocculent precipitate is the crude product of 3TB-2CHO, vacuum filter out the flocculent precipitate, and then use a chromatographic column to filter the flocculent precipitate Isolation was performed to obtain the pure product of 3TB-2CHO.

[0046] The structural characterization data of 3TB-2CHO are as follows:

[0047] Mass spectrum: m / z 380.9 (M+);

[0048] Proton NMR: δ(ppm): 9.96(s, 2H), 8.15~8.0...

Embodiment 2

[0066] 1) Preparation of 3TB-2CHO:

[0067] In the first step, under the protection of nitrogen, add N , N -Dimethylformamide, slowly dropwise adding phosphorus oxychloride, controlling the reaction temperature to 45°C, and stirring for 40 minutes to obtain a reaction solution;

[0068] In the second step, 1,3,5-tri(2 ' -thienyl)-benzene, stirred and reacted for 30 minutes to obtain a reaction solution;

[0069] The third step, after the reaction is over, add distilled water to the above reaction solution for hydrolysis to obtain a flocculent precipitate, vacuum filter out the flocculent precipitate, which is the crude product of 3TB-2CHO, and then separate it with a chromatographic column to obtain 3TB-2CHO pure product.

[0070] The structural characterization data of 3TB-2CHO are as follows:

[0071] Mass spectrum: m / z 380.9 (M+);

[0072] Proton NMR: δ(ppm): 9.96(s, 2H), 8.15~8.05(m, 4H), 8.03(s, 3H), 7.85(d, 1H), 7.71(d, 1H), 7.25(t , 1H);

[0073] Infrared spect...

Embodiment 3

[0090] 1) Preparation of 3TB-2CHO:

[0091] In the first step, under the protection of nitrogen, add N , N - Dimethylformamide, slowly dropwise adding phosphorus oxychloride, controlling the reaction temperature to 65°C, and stirring for 20 minutes to obtain a reaction solution;

[0092] In the second step, 1,3,5-tri(2 ' -thienyl)-benzene, stirred and reacted for 35 minutes to obtain a reaction solution;

[0093] In the third step, after the reaction is completed, distilled water is added to the reaction solution obtained in the second step for hydrolysis to obtain a flocculent precipitate, which is vacuum filtered to remove the flocculent precipitate, which is the crude product of 3TB-2CHO, and then separated by a chromatographic column. The pure product of pure 3TB-2CHO was obtained.

[0094] The structural characterization data of 3TB-2CHO are as follows:

[0095] Mass spectrum: m / z 380.9 (M+);

[0096] Proton NMR: δ(ppm): 9.96(s, 2H), 8.15~8.05(m, 4H), 8.03(s, 3H), ...

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Abstract

The invention provides a star-shaped oligothiophene derivative, a preparation method and application thereof. The derivative is 1, 3-di(2'-(5'-aldehyde)-thienyl)-5-(2'-thienyl)-benzene and is obtained by reacting N, N-dimethylformamide with phosphorus oxychloride, and then, reacting with 1, 3, 5-tri(2'-thienyl)-benzene, hydrolyzing a reaction product, sucking a filtrate and separating the filtrate. The derivative further can be 1, 3, 5-tri(2'-(5'-cyano)-thienyl)-benzene and is obtained by reacting a dichloromethane solution of the 1, 3, 5-tri(2'-thienyl)-benzene with chlorosulfonyl isocyanate, and then, reacting with the N, N-dimethylformamide, hydrolyzing, extracting and purifying a reaction product. The product prepared by the method has good chemical stability and environmental stability, and can be used as an organic electrochromic material to be used for assembling an organic electrochromic device. By using the product, the defects that an inorganic electrochromic material is difficult to form a film, is not suitable to be processed flexibly and cannot be degraded in toxicity are overcome.

Description

technical field [0001] The invention relates to the technical field of organic polymer optoelectronic materials, in particular to star-shaped oligothiophene derivatives and their preparation methods and applications. Background technique [0002] Electrochromism refers to the phenomenon that the optical properties (transmittance, reflectivity or absorptivity) of materials in the ultraviolet-visible or near-infrared region produce stable and reversible changes under the action of an applied electric field. Variety. Materials with electrochromic properties are called electrochromic materials. Electrochromic materials have shown good application prospects in the fields of display, building energy-saving glass, automotive anti-glare rearview mirror, and dimming glass for automobiles or aircrafts. The degree of polymerization and polymerization position can be controlled, and the high-purity oligothiophene with definite molecular weight has a moderate energy gap, wide spectral ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/22C07D333/38C09K9/02G02F1/15
Inventor 赵学全刘平邓文基
Owner 珠海尚明光电有限公司
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