Conjugated polymer of 9,9-dioctyl fluorene and fluorinated quinoxaline
A technology of conjugated polymers and polymers, applied in the field of functional polymers
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Embodiment 1
[0037] Example 1: Preparation of fluoroquinoxaline series for power-deficient units
[0038] With 6-fluoro-5,8-dibromo-2,3-bis(3-octyloxyphenyl)quinoxaline and 6-fluoro-5,8-bis(5-bromo-4-hexylthiophene)- The preparation of 2,3-bis(3-octyloxyphenyl)quinoxaline is an example, and the synthetic route is as follows:
[0039]
[0040] (1) Preparation of 4-fluoro-3,6-dibromo-1,2-phenylenediamine
[0041] 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 00C 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 the solution was washed with 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...
Embodiment 2
[0052] Example 2: Preparation of 9,9-dioctyl-2,7-difluorene borate
[0053] Using 2,7-dibromofluorene as raw material, after synthesizing 9,9-dioctyl-2,7-dibromofluorene according to the traditional method, the compound (5g, 9.1mmol) was added to 70mlTHF under the protection of nitrogen, and the Cool the system to -78°C, add 8.7mL of 2.2M butyllithium dropwise, after the dropwise addition, raise the temperature to 0°C, react at this temperature for 15 minutes, cool the system down to -78°C again, add isopropanol in one go Alcohol borate (4.2g, 21.7mmol), the reaction solution was reacted at room temperature for 24h, poured into ice water, extracted with ether, the organic phase was washed with brine and washed with anhydrous MgSO 4 Dry, concentrate the solvent, and wash the crude product with THF:CH 3 OH=1:1 (volume ratio) recrystallized to obtain 3.1 g of 9,9-dioctyl-2,7-difluorene borate, with a yield of 53%.
[0054] The NMR characterization data are: 1 HNMR (CDCl 3 ,50...
Embodiment 3
[0056] Example 3: Polymer A
[0057]
[0058] The whole reaction was carried out under the protection of nitrogen, 6-fluoro-5,8-bis(5-bromothiophene)-2,3-bis(3-octyloxyphenyl)quinoxaline (263mg, 0.3mmol) and 9, 9-Dioctyl-2,7-difluorene boronate (192.7mg, 0.3mmol) was dissolved in 10ml of toluene, injected into 2.3ml of tetraethylamine hydroxide solution with a mass fraction of 20%, nitrogen gas was passed for 0.5h, and Catalyst tris(dibenzylideneacetone)dipalladium (5.5mg) and ligand tri-o-cresyl phosphine (9.8mg), continue aeration for 0.5h and start heating, reflux reaction for 72h, inject 3.3μl bromobenzene capping, 1h After that, 3.6 mg of phenylboronic acid was added and reacted for 24 hours. The obtained polymer was naturally cooled at room temperature, added dropwise to methanol to settle, filtered, and the collected polymer was dried in a vacuum oven at 50°C for 12 hours. The obtained polymer was sequentially extracted with methanol, n-hexane and chloroform, and co...
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