An organic dye with phenanthrocarbazole as the core and its preparation method, 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, limited application of precious metal dyes, limited precious metal reserves, etc., achieving low cost, environmental friendliness, and avoiding the use of heavy metals Effect
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[0054] The present invention also provides a method for preparing an organic dye with phenanthrocarbazole as the core, comprising:
[0055] The compound shown in formula (IV) is reacted with N,N-dimethylformamide and phosphorus oxychloride, and then with the triphenylamine borate derivative shown in formula (Ⅴ), in palladium acetate, Sphos and potassium phosphate Under the effect of reacting, finally react with cyanoacrylic acid under the effect of ammonium acetate, obtain the organic dye shown in formula (1);
[0056]
[0057] in,
[0058] R 1 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 of the alkoxy groups;
[0060] y is 0;
[0061] x is halogen.
[0062] First, the compound shown in formula (IV) is reacted with N,N-dimethylformamide and phosphorus oxychloride, and the reaction scheme is as follows:
[0063]
[0064] Specifically, first mix the compound represented by formula (IV) with 1,2-dichl...
Embodiment 1
[0105] The preparation of the organic dye of formula (II) structure, 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, 2.00 g of compound 1 was dissolved in 20 mL of 1,2-dichloroethane, and the reaction system was ice-bathed to 0°C, and 0.31 mL of N,N-dimethylformamide and 0.40 mL of phosphorus oxychloride, heated to 40°C and reacted overnight.
[0109] After the reaction, cool the reaction system to room temperature, add 20 mL of water and stir for 2 hours, extract three times with chloroform, combine the organic phases, dry the organic phases with anhydrous sodium sulfate, filter to remove the desiccant, concentrate the filtrate, and use ethyl acetate / petroleum ether (Volume ratio 1 / 20) was used as a developing solvent for column chromatography to obtain 1.76 g of intermediate 2 with a yield of 84%.
[0110] The ...
Embodiment 2
[0134] Preparation of organic dye Ⅲ
[0135] The reaction scheme 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 complete, the temperature of the system was lowered to room temperature. After adding 30 mL of distilled water, extracted three times with chloroform, combined the organic phases, dried the organic phases with anhydrous sodium sulfate, filtered to remove the desiccant, concentrated the filtrate, and used ethyl acetate / petroleum ether (volume ratio 1 / 50) was used as a developing agent for column chromatograph...
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