Terephthaloyl chloride → Carbazole

Participants

Reaction Steps

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.

Provenance & Evidence