Terephthaloyl chloride → Carbazole

To a dry 25 mL dried three-neck round bottom flask was added 0.3320 g (1.206 mmol) carbazole resorcinol (2), 0.06748 g (0.095 mmol) of phenol FIrpic derivative (1) along with 0.2545 g (1.253 mmol) terephthaloyl chloride (4), then 11 mL of dry CHCl3 was added. The suspension was purged under N2, and chilled in a ice salt water bath for 10 min. To this solution, 0.45 mL of dry triethylamine was added using a syringe in a drop wise. Upon the addition of TEA, the milky solution started to become clear. The solution was stirred at ice water temperature for an hour then warmed to room temperature overnight under N2. The solution was diluted with CHCl3 (22 mL) the next day, then washed with equal amounts of NaHCO3 and water three times. The solution was concentrated into 7 mL and anti-solvent precipitated into 50 mL of methanol. The polymer was collected by filtering through M-sized fritted filter. Mw=5093, PDI=1.34.

1. customTo a dry 25 mL dried three-neck round bottom flask
2. customThe suspension was purged under N2
3. temperaturechilled in a ice salt water bath for 10 min
4. additionTo this solution, 0.45 mL of dry triethylamine was added
5. additionUpon the addition of TEA
6. additionThe solution was diluted with CHCl3 (22 mL) the next day
7. washwashed with equal amounts of NaHCO3 and water three times
8. concentrationThe solution was concentrated into 7 mL
9. customanti-solvent precipitated into 50 mL of methanol
10. customThe polymer was collected
11. filtrationby filtering through M-sized fritted filter

ORD record

ord-8d304769e14d4bf5a7341e585aa7ea6b

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07851579B2