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Poly(triphenylamine-benzothiophene/furan) dye and application thereof

A technology of benzothiophene and triphenylamine, which is used in the synthesis and application of functional dyes, can solve the problems of low photoelectric conversion efficiency, and achieve the effects of improving charge mobility, high current density, and improving migration efficiency

Inactive Publication Date: 2015-09-23
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Aiming at the defects of low photoelectric conversion efficiency in the polymer dyes in the prior art, the purpose of the present invention is to improve the structure of the existing poly(triphenylamine-phenothiazine) dyes to obtain a kind of The poly(triphenylamine-benzothiophene / furan) dye of the triphenylamine structural unit of the carboxyl group and the benzothiophene / furan structural unit of the long alkyl chain side chain can be applied to the preparation of relative poly(triphenylamine- Dye-sensitized solar cells with higher photoelectric conversion efficiency and high current density using phenothiazine) dyes

Method used

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  • Poly(triphenylamine-benzothiophene/furan) dye and application thereof
  • Poly(triphenylamine-benzothiophene/furan) dye and application thereof
  • Poly(triphenylamine-benzothiophene/furan) dye and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Synthesis of polymer dye sensitizer with formula II structural unit and its application in dye-sensitized solar cells.

[0054] The synthetic route is as follows:

[0055]

[0056] Synthesis of intermediate (2):

[0057] Add 12.96g 4-bromotriphenylamine, 12.4g 5-aldehyde-2-thiophene boronic acid, and 27.6g anhydrous potassium carbonate into the reaction flask, then add 100mL toluene, 100mL methanol, and add the catalyst ferrocene under the protection of nitrogen. Palladium chloride. Heat to 70°C and track the reaction to completion. The reaction was quenched by adding 150 mL of water and extracted with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate, and filtered. The crude product was separated and purified by column chromatography (silica gel column, eluent: n-hexane / dichloromethane = 4 / 1) to obtain pure Intermediate 2 as a yellow solid with a yield of 60.2%.

[0058] NMR characterization data of intermediate (2):

[0059] 1 H NMR(CDC...

Embodiment 2

[0089] Synthesis of polymer dye sensitizers with structural units of formula III and application in dye-sensitized solar cells.

[0090] The synthetic route is as follows:

[0091]

[0092]

[0093] Synthesis of intermediate (2):

[0094] Add 12.96g 4-bromotriphenylamine, 12.4g 5-aldehyde-2-thiophene boronic acid, and 27.6g anhydrous potassium carbonate into the reaction flask, then add 100mL toluene, 100mL methanol, and add the catalyst ferrocene under the protection of nitrogen. Palladium chloride. Heat to 70°C and track the reaction to completion. The reaction was quenched by adding 150 mL of water and extracted with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate, and filtered. The crude product was separated and purified by column chromatography (silica gel column, eluent: n-hexane / dichloromethane = 4 / 1) to obtain pure Intermediate 2 as a yellow solid with a yield of 60.2%.

[0095] NMR characterization data of intermediate (2):

[0096] ...

Embodiment 3

[0126] Synthesis of polymer dye sensitizer with structural unit of formula IV and its application in dye-sensitized solar cells.

[0127] The synthetic route is as follows:

[0128]

[0129] Synthesis of intermediate (2):

[0130] Add 12.96g 4-bromotriphenylamine, 12.4g 5-aldehyde-2-thiophene boronic acid, and 27.6g anhydrous potassium carbonate into the reaction flask, then add 100mL toluene, 100mL methanol, and add the catalyst ferrocene under the protection of nitrogen. Palladium chloride. Heat to 70°C and track the reaction to completion. The reaction was quenched by adding 150 mL of water and extracted with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate, and filtered. The crude product was separated and purified by column chromatography (silica gel column, eluent: n-hexane / dichloromethane = 4 / 1) to obtain pure Intermediate 2 as a yellow solid with a yield of 60.2%.

[0131] NMR characterization data of intermediate (2):

[0132] 1 H NMR(...

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Abstract

The invention discloses a poly(triphenylamine-benzothiophene / furan) dye and application thereof. The poly(triphenylamine-benzothiophene / furan) dye is provided with a triphenylamine structure unit and a benzothiophene / furan structure monomer, wherein the triphenylamine structure unit contains a conjugated system and a carboxyl group, and the benzothiophene / furan structure monomer is provided with a long alkyl side chain. According to the poly(triphenylamine-benzothiophene / furan) dye, the symmetry and solubility are good; due to a rigid-plane [pi] conjugate skeleton, electron delocalization and intermolecular interaction can be promoted, and charge migration rate can be effectively increased; and by using the poly(triphenylamine-benzothiophene / furan) dye as a dye layer material, dye-sensitized solar cells with high current density and high photoelectric conversion ratio can be prepared.

Description

Technical field [0001] The invention relates to a poly(triphenylamine-benzothiophene / furan) dye and its application, and belongs to the synthesis and application field of functional dyes. Background technique [0002] With people’s declining petroleum resources and increasing energy demand, mankind is facing an increasingly serious energy shortage problem, and people are paying more and more attention to the research of low-cost and renewable solar cells. In the field of solar cells, silicon solar cells occupy a relatively large market share due to their high conversion rate and mature technology. However, the raw materials of silicon solar cells are expensive and the production cost is high. At the same time, it is difficult to further improve the photoelectric conversion efficiency. These shortcomings severely limit The development of silicon solar cells. Especially since 1991 by Switzerland Since the new type of dye-sensitized titanium dioxide nano-film organic solar cell pr...

Claims

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Application Information

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IPC IPC(8): C09B69/10H01G9/20
CPCY02E10/542
Inventor 潘春跃胡祝兵喻桂朋王刚
Owner CENT SOUTH UNIV
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