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Triphenylamine-thiophene organic dyestuff as well as preparation method and application thereof

An organic dye, triphenylamine technology, applied in the direction of organic dyes, organic chemistry, azo dyes, etc., can solve the problems of high battery cost and complicated purification, and achieve the effect of strong power supply performance, high molar absorption coefficient, and inhibition of electronic recombination

Inactive Publication Date: 2014-02-05
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this type of dye contains noble metals, and the purification is complicated, which makes the battery cost higher. In order to avoid the use of noble metal dyes, the current research focus in the world has been placed on efficient organic dye photosensitizers that can replace Ru-based polypyridine complexes.

Method used

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  • Triphenylamine-thiophene organic dyestuff as well as preparation method and application thereof
  • Triphenylamine-thiophene organic dyestuff as well as preparation method and application thereof
  • Triphenylamine-thiophene organic dyestuff as well as preparation method and application thereof

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Embodiment 1

[0027] A preparation method of the triphenylamine-thiophene organic dyes, using aryl bromoaldehyde, tetrakistriphenylphosphine palladium, potassium carbonate and alkoxy substituted triphenylamine borate as raw materials, followed by Suzuki coupling Reaction and Knoevenagel condensation reaction to obtain the target product, the steps are as follows:

[0028] 1) Under the condition of nitrogen protection, in a 100 mL two-necked bottle, add 362 mg of hexyloxy-substituted triphenylamine borolipid (0.5 mmol), 109 mg (0.4 mmol) of bithiophene bromoaldehyde, and 29 mg of tetrasan Phenyl phosphorus (0.025 mmol), potassium carbonate 345 mg (2.5 mmol, 2M) and 30 mL of ethylene glycol dimethyl ether were mixed uniformly, and the obtained mixture was heated to reflux for 8 hours, and the obtained reaction liquid a was cooled to After room temperature, add 15 mL of water to quench, extract with ethyl acetate, separate liquids, dry the organic phase with anhydrous magnesium sulfate, distil...

Embodiment 2

[0040] A preparation method of the triphenylamine-thiophene organic dyes, using aryl bromoaldehyde, tetrakistriphenylphosphine palladium, potassium carbonate and alkoxy substituted triphenylamine borate as raw materials, followed by Suzuki coupling Reaction and Knoevenagel condensation reaction to obtain the target product, the steps are as follows:

[0041] 1) Under the condition of nitrogen protection, in a 100 mL two-necked bottle, add 362 mg of hexyloxy-substituted triphenylamine borolipid (0.5 mmol), 148 mg (0.4 mmol) of dithiophene pyrrole bromaldehyde, and 29 mg of tetra Triphenylphosphine (0.025 mmol), 345 mg of potassium carbonate (2.5 mmol, 2M) and 30 mL of ethylene glycol dimethyl ether were mixed uniformly, and the obtained mixture was heated to reflux for 8 hours, and the obtained reaction liquid a was cooled After reaching room temperature, add 15 mL of water to quench, extract with ethyl acetate, separate the liquids, dry the organic phase with anhydrous magnesi...

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Abstract

The invention provides a triphenylamine-thiophene organic dyestuff. The structural general formula of the triphenylamine-thiophene organic dyestuff is as shown in a formula (I), wherein in the formula (I), R1 is C1-C6 alkoxy, the structural formula of Ar is as shown in a formula (II) or a formula (III), and R2 in the formulas (II) and (III) is C1-C6 alkyls. A preparation method of the triphenylamine-thiophene organic dyestuff comprises the following steps: sequentially carrying out Suzuki coupled reaction and Knoevenagel condensation reaction by using aryl bromal, tetrakis(triphenylphosphine)palladium(0), potassium carbonate and alkoxy substituted triphenylamine boron ester as raw materials, thus obtaining a target product. The triphenylamine-thiophene organic dyestuff can serve as a photosensitizer of a dye-sensitized solar cell. The triphenylamine-thiophene organic dyestuff has the advantages that the distortion spatial structure of alkyl triphenylamine is capable of effectively suppressing the electron recombination and increasing the open-circuit voltage; a thiophene derivative serving as a dyestuff molecule conjugated bridge is capable of ensuring the high molar absorption coefficient and has relatively strong power supply performance, so that the ideal photoelectric conversion efficiency is ensured.

Description

technical field [0001] The invention relates to an organic dye photosensitizer for solar cells, in particular to a triphenylamine-thiophene organic dye and a preparation method and application thereof. Background technique [0002] With the modernization of the world economy, energy and environmental crises are becoming more and more serious. Finding efficient, pollution-free and renewable resources has become the common goal of all countries in the world. As a clean and renewable energy source, solar energy is gradually entering human life, and it is a very effective way to use solar energy for photovoltaic power generation. Since 1991, Swiss scientist M. Grötzel and others reported a new type of solar cell—dye-sensitized solar cell (DSSC), which has the advantages of high efficiency, low cost, low energy consumption, and environmental friendliness, showing strong Prospects for commercial applications. [0003] At present, with Ru-based polypyridine complexes as photosen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/00C07D495/14C07D333/24H01G9/20
CPCY02E10/542
Inventor 梁茂薛松王志辉孙喆武全萍
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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