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Pyrazine-ring-containing organic dyes and preparation method and use thereof
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A technology of organic dyes and pyrazine rings, applied in organic dyes, chemical instruments and methods, methenyl/polymethenyl dyes, etc., can solve problems such as large-scale industrialization restrictions
Inactive Publication Date: 2012-07-04
FUDAN UNIV
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However, expensive precious metal prices and rare precious metal resources have greatly restricted its large-scale industrialization
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Embodiment 1
[0060] Embodiment 1: Dye intermediate 1 preparation of c
[0061] Under nitrogen protection, 1.00 g (2.39 mmol) 1 a (References for synthetic methods Mondal, R.; Miyaki, N.; Becerril, H. A.; Norton, J. E.; Parmer, J.; Mayer, A. C.; Tang, M. L.; Bredas, J. L.; McGehee, M. D.; Bao, Z. N. Chem. Mater. 2009 , 21 , 3618.), 2.43 g (5.00 mmol) 1 b Dissolve in 40 mL DMF, add 110 mg (0.10 mmol) Pd(PPh 3 ) 4 , heated to 85°C, reacted for 5 hours, when the reaction was complete, the reaction system was poured into water, extracted with dichloromethane, the organic phase was washed with water for several times, dried, the solvent was removed, column separation and purification obtained 1.33 g of compound 1c , yield 86%.
Embodiment 2
[0062] Embodiment 2: dye intermediate 1 preparation of d
[0063] Under nitrogen protection, 0.80 g (1.23 mmol) 1 c was dissolved in 30 mL of dichloromethane, added 0.12 mL (1.29 mmol) of phosphorus oxychloride, 0.14 mL (1.81 mmol) of DMF, heated to 70 ° C and refluxed for 8 hours, after the reaction was completed, added saturated sodium acetate and stirred for half The pH of the solution was adjusted to 7 with sodiumhydroxide solution. It was extracted with dichloromethane, the organic phase was washed several times with water, dried, the solvent was removed, and 0.78 g of compound 1d was obtained by column separation and purification, with a yield of 93%.
Embodiment 3
[0064] Embodiment 3: dye intermediate 1 preparation of e
[0065] Under nitrogen protection, 0.74 g (1.09 mmol) 1 d was dissolved in 30 mL chloroform and 10 mL glacial acetic acid, added 0.29 g (1.64 mmol) N-bromosuccinimide, stirred at room temperature for 5 hours, after the reaction was completed, water was added to terminate the reaction, extracted with dichloromethane, organic The phase was washed several times with sodiumhydroxide solution and water, dried, and the solvent was removed, and purified by column separation to obtain 0.69 g of compound 1e with a yield of 83%.
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Abstract
The invention belongs to the technical field of organic photoelectric materials, in particular to pyrazine-ring-containing organic dyes and a synthesis method and use thereof. The pyrazine-ring-containing organic dyes disclosed by the invention have high light trapping capacity; and as the dye molecules take the pyrazine rings as electron-withdrawing groups, the absorption spectrum and fluorescence spectrum of the dyes can be regulated by using different numbers of different aromatic nucleus. Compared with ruthenium dyes, the dyes disclosed by the invention are made of simple, cheap and readily available raw materials and easy to be purified and have the advantages of low cost and easy preparation and the like. In addition, pyrazine and derivatives thereof have high photoelectric properties, such as electronic transmission capacity and strong electron withdrawing capacity, and therefore are high-quality photovoltaic materials; and when applied to dye sensitized solar cells, the dyes can achieve energy conversion efficiency of 8 percent.
Description
technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a class of pure organic dyes containing pyrazine rings, a synthesis method thereof and an application in dye-sensitized solar cells. technical background [0002] Dye-sensitized solar cells (Dye-sensitized solar cells, DSSC) is a new type of solar cell developed based on the principle of plantchlorophyllphotosynthesis. It was first proposed by Professor M. Grötzel of Switzerland in 1991, so it is also called Grötzel Battery. This kind of battery has a simple structure and is mainly composed of a working electrode, an electrolyte and a counter electrode. The working electrode is prepared by sintering a layer of nanoporoustitanium dioxide film on a conductive glass substrate, and adsorbing a layer of photosensitive dye on it. The electrolyte can be liquid, quasi-solid and solid, the most commonly used I 3 - / I - redox couple. The counter...
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