Dithiophene pyrrole bridge-indoline organic dyes as well as preparation method and application thereof

A technology of dithiophene pyrrole bridges and indolines, applied in the fields of organic dyes, organic chemistry, azo dyes, etc., can solve the problems of unfavorable large-scale commercial application of DSSC, low molar absorptivity, and high preparation cost, and achieve Improve the photoelectric conversion efficiency, improve the molar absorptivity, and improve the effect of absorption capacity

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

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Problems solved by technology

Although the photovoltaic properties of ruthenium-based polypyridine dyes are excellent, such dyes use the noble metal ruthenium, which has high preparation costs, and also has the disadvantages of difficult separation and low molar absorptivity, which are not conducive to the large-scale commercial application of DSSCs.

Method used

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  • Dithiophene pyrrole bridge-indoline organic dyes as well as preparation method and application thereof
  • Dithiophene pyrrole bridge-indoline organic dyes as well as preparation method and application thereof
  • Dithiophene pyrrole bridge-indoline organic dyes as well as preparation method and application thereof

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Embodiment 1

[0029] A preparation method of the dithiophenepyrrole bridge-indoline organic dyes, using dithiophenepyrrole bromaldehyde substituted with indoline boroester, tetrakistriphenylphosphine, potassium carbonate and alkoxytriphenylamine as The raw materials are sequentially subjected to Suzuki coupling reaction and Knoevenagel condensation reaction to obtain the target product. The steps are as follows:

[0030] 1) Synthesis of fluorenyl indoline-dithiophene pyrrole carboxaldehyde

[0031] Under the condition of nitrogen protection, in a 100 mL two-necked bottle, add 146 mg (0.2 mmol) of hexyloxytriphenylamine-substituted dithiophene pyrrole bromaldehyde, 267 mg (0.5 mmol) of fluorenyl indoline borolipid, 23.1 mg (0.02 mmol) of tetraphenyltriphenylphosphine, 276 mg (2 mmol) of potassium carbonate solution with a concentration of 2M and 30 mL of ethylene glycol dimethyl ether. After cooling the obtained reaction solution a to room temperature, add 15 mL of water to quench , and the...

Embodiment 2

[0044] A preparation method of the dithiophenepyrrole bridge-indoline organic dyes, using dithiophenepyrrole bromaldehyde substituted with indoline boroester, tetrakistriphenylphosphine, potassium carbonate and alkoxytriphenylamine as The raw materials are sequentially subjected to Suzuki coupling reaction and Knoevenagel condensation reaction to obtain the target product. The steps are as follows:

[0045] 1) Synthesis of tripolyindenyl indoline-dithiophene pyrrole formaldehyde

[0046] Under the condition of nitrogen protection, in a 100 mL two-necked bottle, add 146 mg (0.2 mmol) of hexyloxytriphenylamine-substituted dithiophene pyrrole bromide, 438 mg (0.5 mmol) ), 23.1 mg (0.02 mmol) of tetraphenyltriphenylphosphine, 276 mg (2 mmol) of potassium carbonate solution with a concentration of 2M and 30 mL of ethylene glycol dimethyl ether. After cooling the obtained reaction solution a to room temperature, add 15 mL of water Quenched, then extracted with ethyl acetate, separa...

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Abstract

The invention discloses dithiophene pyrrole bridge-indoline organic dyes with the following structural formula which is shown in the specification, wherein R1 is C1-C6 alkoxy, a structural formula of Ar is (II) or (III); in the formula (II) and (III) which are shown in the specification, R2 is C1-C6 alkyls. A preparation method of the dithiophene pyrrole bridge-indoline organic dyes comprises the following steps of: using indoline boron ester, tetra triphenylphosphine, potassium carbonate and dithiophene pyrrole bromal substituted by alkoxy triphenylamine as materials; and obtaining a target through Suzuki coupling reaction and Knoevenagel condensation reaction in sequence, wherein the target can be used as a photosensitizer of a dye-sensitization solar cell. The preparation method disclosed by the invention has the advantage that a molar absorption coefficient and absorbing ability to light of dye molecules can be effectively improved by introducing the dithiophene pyrrole bridge into the indoline dyes; printed electrons can be effectively compounded and open-circuit voltage can be effectively improved by introducing large steric-hindrance groups into the indoline and the dithiophene pyrrole bridge, so that photoelectric conversion efficiency of the solar cell is improved.

Description

technical field [0001] The invention relates to an organic dye photosensitizer for solar cells, in particular to a dithiophene pyrrole bridge-indoline organic dye and its preparation and application. Background technique [0002] Energy shortage and environmental pollution have become two major problems plaguing human beings, which increasingly restrict the sustainable development of society. Therefore, the development and utilization of renewable energy such as solar energy has become a research hotspot. This energy technology represents the future of green and clean energy. The development direction is in line with the concept of low-carbon and environmental protection. Among them, solar cells are one of the main technologies for utilizing solar energy. 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 friendl...

Claims

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Application Information

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