9-octylcarbazole-fluoroquinoxaline conjugated polymer
A conjugated polymer, fluoroquinoxaline technology, applied in photovoltaic power generation, electrical components, circuits, etc.
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Embodiment 1
[0038] Example 1: The synthesis route of acceptor unit 6-fluoro-5,8-bis(5-bromo-4-hexylthiophene)-2,3-bis(3-octyloxyphenyl)quinoxaline is as follows:
[0039]
[0040] (1) Synthesis of 4-fluoro-3,6-dibromo-phenylenediamine (compound 1)
[0041] 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 purified by n-hexane / ethyl acetate (25:1, v / v) silica gel column to obtain 3.5 g of the product (compound 1) with a yield of 78%.
[0042] (2) Synthesis of 1,2-bis(3-octyloxyphenyl)ethanedione (compound 2)
[0043]Add LiBr (5.25g, 60.4mmol) to a solution of cuprous bromide (4.33g, 30.2mmol) in THF (40ml)...
Embodiment 2
[0052] Example 2: Synthesis of the donor unit 9-octyl-2,7-carbazole boronate
[0053] The synthetic route is as follows:
[0054]
[0055] (1) Synthesis of 9-octyl-2,7-dibromocarbazole (compound 6)
[0056] Add 2,7-dibromocarbazole (12.4g, 38.2mmol) and 300ml DMSO into a four-necked reaction flask with a thermometer and a dropping funnel, and pass through N 2 , add tetrabutylammonium bromide (1.3g), 50% potassium tert-butoxide solution (prepared from 17.2g potassium tert-butoxide and 17.2ml water) in turn under stirring at room temperature, and then add bromooctane ( 7.4g, 38.3mmol), react at room temperature for 5h after addition. Add 200mL of water, filter, wash with water until neutral, dry, recrystallize from ethanol, and dry to obtain 13.5g of white needle-like solid (Compound 6), with a yield of 66.5%.
[0057] (2) Synthesis of 9-octyl-2,7-carbazole boronic acid (compound 7)
[0058] Add compound 6 (7.9g, 14.9mmol) and 150ml THF into a 250mL reaction flask, cool t...
Embodiment 3
[0063] Example 3: Polymer A
[0064]
[0065] The reaction was carried out under the protection of nitrogen. The acceptor unit compound 5 (209.4mg, 0.2mmol) obtained in Example 1, the donor unit compound 8 (106.2mg, 0.2mmol) obtained in Example 2, 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, continue to react for 12h, stop the reaction, cool the system to room temperature, and dilute the reaction solution with methanol Settling and filtering to obtain the 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 a...
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