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A technology of fenocyclopentadiene and conjugated polymers, applied in the field of bisthienocyclopentadiene-fluoroquinoxaline conjugated polymers
Inactive Publication Date: 2015-08-12
XIAN MODERN CHEM RES INST
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However, there have been no reports on the preparation of such materials and their application in photovoltaic cells so far.
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Embodiment 1
[0036] Example 1: Synthesis of 6-fluoro-5,8-dibromo-2,3-bis(3-octyloxyphenyl)quinoxaline, an electrolytic unit
[0037] (1) Preparation of 4-fluoro-3,6-dibromo-1,2-phenylenediamine (compound 2)
[0038]
[0039] 5-Fluoro-4,7-dibromo-2,1,3-benzothiadiazole (5g, 0.016mol) was dissolved in 150ml of absolute ethanol, and NaBH was added in batches at 0°C 4 (11.1g, 0.29mol), and then reacted at room temperature for 20h. After the reaction was over, ethanol was removed by vacuum distillation, 160ml of water was added, extracted with ethyl acetate, the organic phase was washed with saturated brine, and finally anhydrous MgSO 4 dry. Concentrate to remove the organic solvent, and the obtained crude product is separated by n-hexane / ethyl acetate (the volume ratio of n-hexane to ethyl acetate is 25:1) silica gel column to obtain 4-fluoro-3,6-dibromo-1 ,2-phenylenediamine 3.5g, yield 78%.
[0040] (2) Preparation of 1,2-bis(3-octyloxyphenyl)ethanedione (compound 5)
[0041]
[0...
Embodiment 2
[0047] Example 2: Synthesis of 6-fluoro-5,8-dibromo-2,3-bis(4-octyloxyphenyl)quinoxaline (compound 8)
[0048]
[0049] Using 4-fluoro-3,6-dibromo-1,2-phenylenediamine and 1,2-bis(4-octyloxyphenyl)ethanedione as raw materials, according to the method of synthesizing compound 6, the target Product, yield 82%.
Embodiment 3
[0050] Example 3: Synthesis of 6,7-difluoro-5,8-dibromo-2,3-bis(3-octyloxyphenyl)quinoxaline
[0051] (1) Preparation of 4,5-difluoro-3,6-dibromo-1,2-phenylenediamine (compound 10)
[0052]
[0053] 5,6-difluoro-4,7-dibromo-2,1,3-benzothiadiazole (10g, 0.031mol) was dissolved in 300ml absolute ethanol, and NaBH was added in batches at 0°C 4 (22.2g, 0.59mol), and then reacted at room temperature for 20h. After the reaction, ethanol was removed by vacuum distillation, 200ml of water was added, extracted with ethyl acetate, the organic phase was washed with saturated brine, and finally anhydrous MgSO 4 dry. The crude product obtained by concentration was chromatographed on a silica gel column with n-hexane / ethyl acetate (the volume ratio of n-hexane to ethyl acetate was 20:1) to obtain 4,5-difluoro-3,6-dibromo-1,2 - phenylenediamine 6.1 g, yield 65%.
[0054] (2) Preparation of 6,7-difluoro-5,8-dibromo-2,3-bis(3-octyloxyphenyl)quinoxaline (compound 11)
[0055]
[0056...
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Abstract
The present invention aims to use of the electron-withdrawing characteristic of fluorine atom, exploit a D-A-D type donor polymeric material containing chloroquinoxaline, and reduce the HOMO energy level of the polymeric material. The invention discloses a conjugated polymer of dithiophene pentalene and chloroquinoxaline, which comprises a structural general formula shown as a following graph. In the formula, R1 is H or F atom; R2 is alkylene group of straight chain or branched chain with meta-carbon atom numbers or para-carbon atom numbers being 4-20, or, is 2-alkylthiophene or 2,3-dialkyl thienyl group of straight chain or branched chain with carbon atom numbers being 4-20. Compared with corresponding non-fluoro polymer, the HOMO energy level of single fluoropolymer is lower by 0.02-0.2eV than that of the non-fluoro polymer, and the HOMO energy level of the double fluoro polymer is lower by 0.05-0.3eV than that of the non-fluoro polymer.
Description
technical field [0001] The invention belongs to the field of functional polymers, in particular to a bisthienocyclopentadiene-fluoroquinoxaline conjugated polymer. Background technique [0002] Today's energy problem is the primary issue of economic development in all countries in the world. It has always been the goal of scientists to directly convert solar energy into electrical energy and thermal energy for the benefit of mankind. One of the effective ways to develop low-cost solar cells is to start with materials, and the performance of solar cells can be effectively improved through the modification of materials. Polymer solar cells have obvious advantages such as low cost, good flexibility, and easy preparation. Therefore, this type of solar cell has important development and application prospects, and has become the frontier and focus of photovoltaic cell research. At present, polymer batteries still have the problem of low conversion efficiency. The development of ...
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