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Double-strand phenothiazine dye with benzotriazole led into Pi bridge and application thereof in preparation of dye-sensitized solar cells

A benzotriazole and solar cell technology, applied in thiazine dyes, organic dyes, photovoltaic power generation, etc., can solve problems such as difficulty in cost reduction, limitation of large-scale practical application, difficulty in separation and purification of ruthenium polypyridine complexes, etc. To achieve the effect of increasing adsorption capacity, improving photoelectric conversion efficiency, and cheap raw materials

Active Publication Date: 2014-05-14
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 application.
At present, there is no use of phenothiazine as an electron donor, the electron-deficient group of benzotriazole is introduced into the π bridge, and cyanoacetic acid is a double-chain phenothiazine dye with an electron acceptor and an anchoring group. to report

Method used

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  • Double-strand phenothiazine dye with benzotriazole led into Pi bridge and application thereof in preparation of dye-sensitized solar cells
  • Double-strand phenothiazine dye with benzotriazole led into Pi bridge and application thereof in preparation of dye-sensitized solar cells
  • Double-strand phenothiazine dye with benzotriazole led into Pi bridge and application thereof in preparation of dye-sensitized solar cells

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Synthesis of double chain phenothiazine dye HZ containing benzotriazole in π bridge

[0041] (1) Synthesis of compound 2

[0042]

[0043] Under the protection of argon, with 50mLTHF as solvent, add 1.43g (3.67mmol) compound 1, 11mL2M K 2 CO 3 solution and 1.127g (8.81mmol) 2-thiophene boronic acid, and then add 211mg of Pd (PPh 3 ) 4 Be a catalyst. Then the temperature was raised to 70°C for 24h. After cooling to room temperature, the reaction solution was poured into water, extracted with 200 mL of DCM, and washed twice with 200 mL of water. After drying, filtering, and removing the solvent, the crude product was separated and purified by column chromatography, using ethyl acetate:petroleum ether (1:20) as the mobile phase, to obtain a light yellow product with a yield of 84%. Melting point: 74-76°C. NMR: 1 H NMR (400MHz, CDCl 3 )δ8.09-8.08(m,2H),7.61(s,2H),7.37-7.36(m,2H),7.19-7.17(m,2H),4.80(t,J=7.2Hz,2H),2.22 -2.15(m,2H),1.45-1.34(m,2H),1.33-1.27(m,6H)...

Embodiment 2

[0060] To the ultraviolet-visible absorption spectrum test of embodiment 1, ultraviolet-visible absorption spectrum is as figure 1 shown.

[0061] Solvent: tetrahydrofuran / dichloromethane (1:1)

[0062] Concentration: 2×10 -5 m

[0063] Temperature: room temperature

[0064] Instrument: Shimadzu UV-2450 UV-Vis spectrophotometer

[0065] The resulting data are summarized in Table 1

[0066] The ultraviolet-visible spectral data of table 1 embodiment 1 dyestuff

[0067] dye

[0068] From figure 1 It can be seen from Table 1 that the maximum absorption wavelength of the dye HZ in the mixed solvent of tetrahydrofuran / dichloromethane (1:1) is 489nm, and this peak is caused by the intramolecular charge transfer (ICT) of the dye. The corresponding molar extinction coefficient of the dye HZ at the maximum absorption wavelength reaches 86208M -1 cm -1 , so that the data is much higher than that of common pure organic dyes; this indicates that this series of dyes has ...

Embodiment 3

[0070] The making of dye-sensitized solar cell among the present invention is as follows:

[0071] (1) Pretreatment of conductive glass (FTO): The conductive glass is fully cleaned with ultrasonic waves in degreasing agent, absolute ethanol and deionized water in sequence, and then dried for later use;

[0072] (2) TiO 2 Preparation of nanocrystalline particles and their slurry: at room temperature, 10mL Ti(OBu) 4 After stirring the mixture with 20mL of EtOH for 10 minutes, add 18mL of acetic acid and 50mL of deionized water to the above solution under vigorous stirring and keep stirring for 1h, then transfer the mixture into an autoclave at 230°C for 12h, and naturally cool to room temperature , filter the resulting suspension, wash with deionized water and ethanol several times respectively, and dry in an oven at 50°C for 6h to dry to obtain TiO with a particle size of about 18-20nm. 2 Nanocrystalline particles;

[0073] (3) Take TiO 2 Add 1.0g of nanocrystalline particl...

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Abstract

The invention discloses a double-strand phenothiazine dye with benzotriazole led into a Pi bridge and an application thereof in the preparation of dye-sensitized solar cells, and belongs to the field of photoelectric converting material application in fine chemical engineering. A preparation method of the double-strand phenothiazine dye with the benzotriazole led into the Pi bridge comprises the following steps: leading benzotriazole which is an electron-deficient group into the Pi bridge by using phenothiazine as an electron donor, and synthesizing a series of double-strand phenothiazine dyes by using cyanoacetic acid as an electron acceptor and anchoring group. The double-strand phenothiazine dye is capable of increasing adsorbing capacity and inhibiting the aggregation of the dye. In addition, benzotriazole which is an electron-deficient additional acceptor is led into the Pi bridge and plays a role in widening an absorption spectrum. In consideration of the two effects, the double-strand phenothiazine dye has more excellent performances than common phenothiazine dye under the same conditions and can be used for effectively improving the photoelectric conversion efficiency of the 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 double-chain phenothiazine dyes with benzotriazole introduced into π bridges and their application in the preparation of 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. The cost ...

Claims

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Application Information

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IPC IPC(8): C09B21/00H01G9/20
CPCY02E10/542
Inventor 曹德榕黄祖胜
Owner SOUTH CHINA UNIV OF TECH
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