Organic dyes having rigid donor, process for producing the same, and dye-sensitized solar cell
a solar cell and organic dye technology, applied in the field of organic dyes with rigid donors and processes for producing the same, can solve the problems of poor efficiency, low power conversion efficiency of devices made from purely organic dyes, and sharp increase in environmental problems accompanied by ore-based energy consumption, and achieve the effect of high power conversion efficiency
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example 1
[0094]The reaction scheme is shown as follows:
[0095]wherein R1′ is
R2′ is hexyl. Also, in the following Examples, they are the same as in this Example.
1.1 Synthesis of the Intermediate 2
[0096]In a three-necked round-bottom flask, 2.00 g of the compound 1 was dissolved in 20 mL N,N-dimethyl formamide. 4.33 g 2-hexyldecyl-4-methylbenzenesulfonate and 2.13 g potassium hydroxide were added to the reaction system, and then the mixture is heated to 100° C. and reacted under stirring, and the reaction is kept overnight.
[0097]After the reaction was finished, the reaction system was cooled to room temperature, and 20 mL water was added thereto. The resultant mixture solution was extracted with chloroform three times. The organic phases were combined and dried over anhydrous sodium sulfate. The desiccant was removed by filtration. The filtrate was concentrated, and then was separated by column chromatography with petroleum ether (boiling point: 60-90° C.) as the eluent to give 3.91 g of the in...
example 2
[0143]The reaction scheme is shown as follows:
2.1 Synthesis of the Intermediate 14
[0144]In a three-necked round-bottom flask, 1.00 g of the intermediate 10 from Example 1, 184 mg of the compound 13 and 871 mg potassium phosphate were dissolved in a mixed solvent of 20 mL 1,4-dioxane and 4 mL water. 4 mg Pd(OAc)2 as the catalyst and 8 mg 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (Sphos) as the organophosphine ligand were added under the protection of argon. The reaction system was heated to 45° C., and the reaction is kept for 12 hours.
[0145]After the reaction was finished, the reaction system was cooled to room temperature, and 20 mL water was added thereto. The resultant mixture solution was extracted with chloroform three times. The organic phases were combined and dried over anhydrous sodium sulfate. The desiccant was removed by filtration. The filtrate was concentrated, and then was separated by column chromatography with ethyl acetate / petroleum ether (volume ratio: 1 / 50) ...
example 3
[0161]The reaction scheme is shown as follows:
3.1 Synthesis of the Intermediate 18
[0162]In a three-necked round-bottom flask, 1.00 g of the intermediate 10 from Example 1, 399 mg of the compound 17 and 871 mg potassium phosphate were dissolved in a mixed solvent of 20 mL 1,4-dioxane and 4 mL water. 4 mg Pd(OAc)2 as the catalyst and 8 mg 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (Sphos) as the organophosphine ligand were added under the protection of argon. The reaction system was heated to reflux, and the reaction is kept for 12 hours.
[0163]After the reaction was finished, the reaction system was cooled to room temperature, and 20 mL water was added thereto. The resultant mixture solution was extracted with chloroform three times. The organic phases were combined and dried over anhydrous sodium sulfate. The desiccant was removed by filtration. The filtrate was concentrated, and then was separated by column chromatography with ethyl acetate / petroleum ether (volume ratio: 1 / 50) ...
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