Organic dye centered on phenanthrene and carbazole, preparation method thereof and organic dye sensitized solar cell
An organic dye, phenanthrocarbazole technology, applied in the field of organic dye-sensitized solar cells, can solve the problems of specific efficiency gap, limit the application of noble metal dyes, and limited reserves of precious metals, and achieve low cost, environmental friendliness, and avoid the use of heavy metals Effect
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[0054] The present invention also provides a preparation method of organic dyes with phenanthrocarbazole as the core, including:
[0055] The compound represented by formula (IV) is reacted with N,N-dimethylformamide and phosphorus oxychloride, and then with the triphenylamine borate derivative represented by formula (Ⅴ), in palladium acetate, Sphos and potassium phosphate It reacts under the action, and finally reacts with cyanoacrylic acid under the action of ammonium acetate to obtain the organic dye represented by formula (1);
[0056]
[0057] among them,
[0058] R 1 Selected from C 1 ~C 18 alkyl;
[0059] R 2 , R 3 Independently selected from H, C 1 ~C 18 Alkyl or C 1 ~C 18 Any one of alkoxy groups;
[0060] y is 0;
[0061] x is halogen.
[0062] First, the compound represented by formula (IV) is reacted with N,N-dimethylformamide and phosphorus oxychloride, the reaction route is as follows:
[0063]
[0064] Specifically, first mix the compound represented by formula (IV) with 1,...
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[0104] Example 1
[0105] For the preparation of organic dyes of formula (II), the synthetic route is as follows:
[0106]
[0107] Compound 1 was synthesized according to references (W. Jiang, H. Qian, Y. Li, Z. Wang, J. Org. Chem. 2008, 73, 7369.).
[0108] In a dry Schlenk reaction flask, dissolve 2.00 g of compound 1 in 20 mL of 1,2-dichloroethane, ice bath the reaction system to 0°C, and add 0.31 mL of N,N-dimethylformamide to the reaction system And 0.40mL phosphorous oxychloride, heated to 40°C and reacted overnight.
[0109] After the reaction, the reaction system was cooled to room temperature, 20 mL of water was added and stirred for 2 hours, and chloroform was extracted three times. The organic phases were combined and dried with anhydrous sodium sulfate. The desiccant was removed by filtration, the filtrate was concentrated, and ethyl acetate / petroleum ether was used. (Volume ratio 1 / 20) Column chromatography was used as a developing solvent to obtain 1.76 g of Intermedia...
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[0133] Example 2
[0134] Preparation of organic dye Ⅲ
[0135] The reaction route is as follows:
[0136]
[0137] Synthesis of Intermediate 5:
[0138] Compound 4 was synthesized according to literature (R. Li, J. Liu, N. Cai, M. Zhang and P. Wang, J. Phys. Chem. B, 2010, 114, 4461.).
[0139] In a dry Schlenk reaction flask, 500 mg of compound 4 and 218 mg of triisopropylsilylacetylene were dissolved in 20 ml of toluene, and 67 mg of Pd(PPh 3 ) 2 Cl 2 , 18mg cuprous iodide and 2mL triethylamine. The reaction system was heated to reflux overnight.
[0140] After the reaction was completed, the temperature of the system was lowered to room temperature, after adding 30 mL of distilled water, chloroform was extracted three times, and the organic phases were combined, dried with anhydrous sodium sulfate, filtered to remove the desiccant, and the filtrate was concentrated and used ethyl acetate / petroleum ether (volume ratio 1 / 50) Column chromatography was used as a developing solvent to o...
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