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Organic dye containing benzothiadiazole-thienocyclopenta and applications of organic dye in dye-sensitized solar cells

A technology of benzothiadiazole and organic dyes, applied in organic dyes, azo dyes, photovoltaic power generation and other directions, can solve the problem of poor light absorption ability, achieve high molar absorption coefficient, wide spectral response range, narrow molecular energy gap effect

Active Publication Date: 2014-09-03
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to provide organic dyes containing benzothiadiazole-thienocyclopentadiene and their application in dye-sensitized solar cells in order to solve the problem of poor light absorption ability of existing organic dyes

Method used

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  • Organic dye containing benzothiadiazole-thienocyclopenta and applications of organic dye in dye-sensitized solar cells
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  • Organic dye containing benzothiadiazole-thienocyclopenta and applications of organic dye in dye-sensitized solar cells

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Embodiment 1: the preparation of organic dye III

[0018] The synthetic route is as follows:

[0019]

[0020] The raw materials 1 and 4 used in this example, as well as other reagents can be obtained commercially. Raw material 7 was prepared according to literature Li, R.; Liu, J.; Cai, N.; Zhang, M.; Wang, P.J.Phys.Chem.B 2010,114,4461.

[0021] Synthesis of Intermediate 2:

[0022] Add 5.50 g of raw material 1 and 50 ml of n-butanol into a 100 ml round bottom flask, slowly add 1.5 ml of concentrated sulfuric acid dropwise, heat the reaction system under reflux for 20 hours and cool to room temperature, add 50 ml of water to the reaction system, and wash with chloroform (3×50 ml) extracted three times, combined the organic phases, dried with anhydrous sodium sulfate and filtered, and the crude product obtained after concentrating the filtrate was passed through a silica gel column with ethyl acetate / petroleum ether (volume ratio 1 / 20) as eluent After chromatogra...

Embodiment 2

[0062] Embodiment 2: the preparation of organic dye IV

[0063] The synthetic route is as follows:

[0064]

[0065] Raw material 12 was prepared according to literature Li, R.; Liu, J.; Cai, N.; Zhang, M.; Wang, P.J.Phys.Chem.B 2010, 114, 4461.

[0066] The synthesis of intermediates 3 and 5 was obtained with reference to the preparation method in Example 1;

[0067] Synthesis of intermediate 11:

[0068] Add 4 grams of intermediate 3, 4.6 grams of 4,7-dibromobenzothiadiazole, 16.4 grams of sodium carbonate and 280 milliliters of ethanol / benzene / water mixed solvent (volume ratio 1 / 4 / 2) in a 500 ml round bottom flask ), under the protection of argon, add 0.3 g of tetrakistriphenylphosphopalladium, heat the reaction system to reflux for 2 hours, then cool to room temperature, add 200 ml of water, extract three times with chloroform (3×100 ml), combine the organic phases, and use After drying with anhydrous sodium sulfate and filtering, the crude product obtained after con...

Embodiment 3

[0093] Nano TiO 2 The structural double-layer membrane electrode was immersed in acetonitrile / tert-butanol (volume ratio, 1:1) solution containing 100 micromoles per liter of dye III for 12 hours, and then the glass electrode spin-coated with nano-platinum was passed through a 35 microns thick Hot melt ring and TiO 2 The structural double-layer film electrode is heated and sealed, and finally the electrolyte is injected into the gap between the two electrodes, which constitutes a dye-sensitized solar cell. The performance structure of the dye-sensitized solar cells obtained by the test is shown in Table 1.

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Abstract

The invention provides an organic dye containing benzothiadiazole-thienocyclopenta and applications of the organic dye in dye-sensitized solar cells, and belongs to the field of organic dye. Triphenylamine is selected as a electron donor, benzoic acid is selected as an acceptor, and benzothiadiazole-thienocyclopenta unit is selected as a connecting unit. Benzothiadiazole is a structure unit with excellent electron withdrawing performance, and thienocyclopenta is an electron-rich structure unit, so that the introduction of the two units into the organic dye is capable of adjusting molecular energy level of the organic dye significantly, and decreasing molecular energy gaps. The invention also provides the applications of the organic dye in dye-sensitized solar cells. It is confirmed by experiments that: the open-circuit voltage of a dye-sensitized solar cell prepared by using the organic dye can reach to 886mV, the short-circuit photocurrent reaches to 16.17mA / cm<2>, and the power transformation efficiency reaches to 10.4%.

Description

technical field [0001] The invention belongs to the technical field of organic dyes, in particular to an organic dye containing benzothiadiazole-thienocyclopentadiene and its application in dye-sensitized solar cells. Background technique [0002] At present, solar cells on the market are mainly silicon solar cells, among which crystalline silicon solar cells are the most widely used technology, accounting for more than 80% of solar cells. However, it has the disadvantages of high manufacturing cost, harsh process conditions, high energy consumption and serious pollution in the silicon refining process. Therefore, based on organic photoelectric functional materials, cheap excitonic solar cells have received extensive attention and research at home and abroad. year 1991, The research group used the trinuclear ruthenium dye RuL reported by Amadelli et al. 2 (μ-(CN)Ru(CN)L' 2 ) 2 (L=2,2′-bipyridine-4,4′-dicarboxylic acid, L′=2,2′-bipyridine) as a sensitizer adsorbed on th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B57/00H01G9/20
CPCY02E10/542
Inventor 王鹏许名飞马文涛
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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