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Three-dimensionally prolonged conjugated chain phenothiazine dyes and application to dye-sensitized solar cells thereof

A dye-sensitized, solar cell technology, applied to three-way extended conjugated chain phenothiazine dyes and its application in dye-sensitized solar cells, can solve the limitations of large-scale practical application, separation of ruthenium polypyridine complexes Difficulty in purification, difficulty in reducing the cost of DSSCs, etc., to achieve the effect of improving photoelectric conversion efficiency, cheap raw materials, and enhancing absorption

Active Publication Date: 2014-01-08
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, ruthenium is a rare and precious metal, and the separation and purification of ruthenium polypyridine complexes is also quite difficult, and the cost of DSSCs is difficult to reduce, which limits its large-scale practical use.
At present, there are no reports of dyes with three-way extended conjugated chain phenothiazine as electron donor and dicyanoacetic acid as electron acceptor.

Method used

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  • Three-dimensionally prolonged conjugated chain phenothiazine dyes and application to dye-sensitized solar cells thereof
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  • Three-dimensionally prolonged conjugated chain phenothiazine dyes and application to dye-sensitized solar cells thereof

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Experimental program
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Effect test

Embodiment 1

[0039] Synthesis of three-way extended conjugated chain phenothiazine dye PPFA

[0040] The following reactions were all carried out in a dry environment under nitrogen protection.

[0041] (1) Synthesis of compound 2

[0042]

[0043] 0.81 g (2 mmol) of compound 1 was dissolved in 150 ml of chloroform and kept at 0°C. Then 20ml of chloroform solution dissolved with 0.22ml (4mmol) of liquid bromine was added dropwise into the flask while keeping the temperature at around 0°C. The reaction was stirred for 8h. Stirring was continued for 1 h after adding a dilution of NaOH. Adding salt water is conducive to stratification. Use 200ml CH 2 Cl 2 Extract and wash twice with 200ml of water. After drying, filtering, and removing the solvent, the crude product was separated and purified by column chromatography (dichloromethane as mobile phase) to obtain a bright green product with a yield of 92.5%. Melting point: 107–108°C. NMR 1 H NMR (CDCl 3 ,400MHz,δ,ppm):7.25–7.22(m,2...

Embodiment 2

[0057] Synthesis of three-way extended conjugated chain phenothiazine dye PPTA

[0058] All reactions were carried out in a dry environment under nitrogen protection

[0059]

[0060] 2.25g (4mmol) compound 2 and 2.21g (16mmol) K 2 CO 3 and Pd(PPh 3 ) 4 (10mole%) was added to 40ml of DMF, stirred and reacted at 40°C for 0.5h under the protection of argon. Then, 0.49 g (3.5 mmol) of 5-formyl-2-thiopheneboronic acid dissolved in 5 ml of DMF was slowly added dropwise under stirring, and after the addition was completed, the temperature was raised to 80° C. for 48 h. Cool after the reaction is over, pour the reaction solution into 200ml water, and use CH 2 Cl 2 extraction. The organic layer was washed several times with water to completely remove DMF. After drying and concentration, the crude product was separated and purified by column chromatography (petroleum ether and dichloromethane (1:1) as mobile phase) to obtain 0.87 g of orange product with a yield of 36.9%. M...

Embodiment 3

[0071] The ultraviolet-visible absorption spectrum / fluorescence spectrum test of embodiment 1 and embodiment 2 dyestuff, ultraviolet-visible absorption spectrum and fluorescence emission spectrogram are respectively figure 1 , figure 2 shown.

[0072] Solvent: tetrahydrofuran / dichloromethane (1:1)

[0073] Concentration: 2×10 -5 m

[0074] Temperature: room temperature

[0075] Instruments: Shimadzu UV-2450 UV-visible scenery photometer, Hitachi F-4500 fluorescence spectrometer

[0076] The resulting data are summarized in Table 1

[0077] dye Maximum UV / Vis Absorption Wavelength (nm) Maximum fluorescence emission wavelength (nm) Example 1 358,473 596 Example 2 359,476 571

[0078]The maximum ultraviolet / visible absorption wavelength and the maximum fluorescence emission wavelength (nm) data of dyestuff in table 1 embodiment 1 and 2

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Abstract

The invention discloses three-dimensionally prolonged conjugated chain phenothiazine dyes and an application to dye-sensitized solar cells thereof, and belongs to the field of photoelectric conversion material application in fine chemical engineering. According to the invention, an aromatic nucleus is introduced at 3 position of phenothiazine; phenyl rings are introduced at 7 and 9 positions; the conjugated chain is prolonged at the three directions simultaneously; thus the three-dimensionally prolonged conjugated chain phenothiazine is used as an electron donor; cyanoacetic acid is used as an electron receptor; and a series of three-dimensionally prolonged conjugated chain phenothiazine dyes are synthesized. The three-dimensionally prolonged conjugated chain phenothiazine dyes have stronger light-capturing capability in visible region, thus have superior performance to common phenothiazine dyes under the same conditions, and can effectively improve the photoelectric conversion efficiency of dye-sensitized solar cells.

Description

technical field [0001] The invention relates to the technical field of phenothiazine and dye-sensitized solar cells, in particular to a class of three-way extended conjugated chain phenothiazine dyes and their application in dye-sensitized solar cells. technical background [0002] Dye-sensitized solar cells (DSSCs) are a novel device for converting solar energy into electricity. Compared with traditional silicon-based solar cells, this type of cell has the advantages of simple structure and low manufacturing cost, and is a type of photoelectric conversion device with broad application prospects. The structural design of dyes is crucial for the photoelectric conversion efficiency of such cells. Currently, ruthenium polypyridine complexes have the highest photoelectric conversion efficiency. However, ruthenium is a rare and precious metal, and the separation and purification of ruthenium polypyridine complexes is also quite difficult, and the cost of DSSCs is difficult to r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B21/00H01G9/20
CPCY02E10/542
Inventor 曹德榕成远高
Owner SOUTH CHINA UNIV OF TECH
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