Asymmetric dye molecule with combined five-membered ring as core and preparation method of asymmetric dye molecule
An asymmetric, five-membered ring technology, applied in the field of chemical synthesis, can solve the problems of shedding, insufficient adsorption force, easy self-degradation of organic sensitizers, etc., and achieves improved conversion efficiency, wide absorption range, good thermal stability and The effect of chemical stability
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Embodiment 1
[0025] What this example prepared was the dye molecule described in general formula (1), wherein R1 is R2 is The reaction steps are as follows:
[0026] (1) Dissolve 7.8g (31.2mmol) of 2,5-dibromoaniline in 16ml of glacial acetic acid, and add 6ml of 96% sulfuric acid dropwise. Add 16ml dropwise containing 6.42g NaNO 2 of aqueous solution. Stir at 0°C for 1 hour, then add 12ml of an aqueous solution containing 3.6g of urea dropwise to make the excess NaNO 2 Total response. Then 15.48g (93.4mmol) of KI aqueous solution was added dropwise, and the product was extracted with dichloromethane after reacting for 1 hour. After drying, it was chromatographed with petroleum ether to obtain 7.92g of white solid with a yield of 70%.
[0027] (2) Dissolve 4.34g (12.0mmol) of 2,5-dibromophenyliodide and 2.56g (14.4mmol) of 2-ethynyl-4-pentyl-thiophene in 140ml of tetrahydrofuran and triethyl ether at a volume ratio of 1:1 The amine mixture was stirred under argon for 40 minutes. A...
Embodiment 2
[0034] What this example prepared was the dye molecule described in general formula (1), wherein R1 is R2 is The reaction steps are as follows:
[0035] (1) Dissolve 2.60 g (10.4 mmol) of 2,5-dibromoaniline in 5 ml of glacial acetic acid, and add 2 ml of 96% sulfuric acid dropwise. Add 5ml dropwise containing 2.14g NaNO 2 of aqueous solution. Stir at 0°C for 1 hour, then add 4ml of an aqueous solution containing 1.2g of urea dropwise to make the excess NaNO 2 Total response. Then 5.16g (31.1mmol) KI aqueous solution was added dropwise, and the product was extracted with dichloromethane after reacting for 1 hour. After drying, it was chromatographed with petroleum ether to obtain 2.6g of white solid with a yield of 69%.
[0036] (2) 2.17g (6.0mmol) 2,5-dibromophenyl iodide and 1.24g (7.2mmol) pentylphenylacetylene are dissolved in 80ml of a mixed solution of tetrahydrofuran and triethylamine with a volume ratio of 1:1. Stir under argon for 40 minutes. Add 68 mg of trip...
Embodiment 3
[0043] What this example prepared was the dye molecule described in general formula (1), wherein R1 is R2 is The reaction steps are as follows:
[0044] (1) Dissolve 5.20 g (20.8 mmol) of 2,5-dibromoaniline in 10 ml of glacial acetic acid, and add 4 ml of 96% sulfuric acid dropwise. Add 10ml dropwise containing 4.28g NaNO 2 of aqueous solution. Stir at 0°C for 1 hour, then add 8ml of an aqueous solution containing 2.4g of urea dropwise to make the excess NaNO 2 Total response. Then 10.32g (62.2mmol) of KI aqueous solution was added dropwise, and the product was extracted with dichloromethane after reacting for 1 hour. After drying, it was chromatographed with petroleum ether to obtain 5.2g of white solid with a yield of 68.9%.
[0045] (2) 3.62g (10.0mmol) 2,5-dibromophenyl iodide and 2.26g (12.0mmol) pentyloxyphenylacetylene are dissolved in 120ml of a mixed solution of tetrahydrofuran and triethylamine with a volume ratio of 1:1, Stir under argon for 45 minutes. Add...
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