Conjugated polymer of 9-heptadecylcarbazole and fluoroquinoxaline
A technology of heptadecylcarbazole and conjugated polymers, applied in the field of functional polymer materials
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Embodiment 1
[0045] Example 1: Synthesis of acceptor unit 6-fluoro-5,8-bis(5-bromothiophene)-2,3-bis(3-octyloxyphenyl)quinoxaline
[0046] The synthetic route is as follows:
[0047]
[0048] (1) Synthesis of 4-fluoro-3,6-dibromo-1,2-phenylenediamine (compound 1)
[0049] 5-Fluoro-4,7-dibromo-2,1,3-benzothiadiazole (5g, 16mmol) was dissolved in absolute ethanol (150ml), and NaBH was added in batches at 0°C 4 (11.1g, 290mol), and then reacted at room temperature for 20h. After the reaction was finished, concentrate to remove ethanol, add 160ml of water, extract with ethyl acetate, wash the organic phase with saturated brine, anhydrous MgSO 4 Drying and concentration gave the crude product, which was chromatographed on a silica gel column with n-hexane / ethyl acetate (25:1, v / v) to obtain 3.5 g of the product (compound 1) with a yield of 78%.
[0050] (2) Synthesis of 1,2-bis(3-octyloxyphenyl)ethanedione (compound 2)
[0051] Add LiBr (5.25g, 60.4mmol) to a solution of cuprous bromide ...
Embodiment 2
[0059] Example 2: Synthesis of the donor unit 9-heptadecyl-2,7-carbazole borate
[0060] The synthetic route is as follows:
[0061]
[0062] (1) Synthesis of 9-heptadecyl-2,7-dibromocarbazole (compound 6)
[0063] 2,7-dibromocarbazole (20.3g, 62.5mmol), potassium hydroxide (20.3g, 362.5mmol) and DMSO (160mL) were added in a 500mL reaction flask, and N 2 After heating up to 40°C, 200ml of DMSO solution of 9-heptadecyl-p-toluenesulfonate (38.6g, 94.1mmol) was added dropwise for 2h, and reacted at 40°C for 6h after dropping. Then the reaction solution was poured into 700 mL of water, extracted with n-hexane, the organic phases were combined, washed with saturated brine until neutral, and dried overnight with anhydrous magnesium sulfate. After filtration and concentration, the crude product was obtained, which was recrystallized from industrial ethanol to obtain 18.2 g of white solid (compound 6), with a yield of 51.8%.
[0064] (2) Synthesis of 9-heptadecyl-2,7-carbazole b...
Embodiment 3
[0067] Example 3: Polymer A
[0068]
[0069] The reaction was carried out under the protection of nitrogen. The acceptor unit compound 5 (175.8 mg, 0.2 mmol) obtained in Example 1, the donor unit compound 7 (131.5 mg, 0.2 mmol) obtained in Example 2, and tetraethyl hydroxide Ammonium (20%, 1.5ml) and toluene (15ml) were added to a dry two-necked flask, ventilated for 0.5h, and the catalyst tris(dibenzylideneacetone)dipalladium (3.7mg) and the ligand tri-o-cresylphosphine were added (6.5mg), continue to ventilate for 0.5h, then start heating, after reflux reaction for 60h, add 2.2ul bromobenzene, add 2.4mg phenylboronic acid after 1h, react for another 12h, stop the reaction, cool the system to room temperature, and dilute the reaction solution with methanol Settling and filtering to obtain a polymer, drying in a vacuum oven at 50°C for 12 hours, performing Soxhlet extraction with methanol, n-hexane, and chloroform in sequence, concentrating the chloroform extract, settling...
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