Sodium Carbonate → Tetraphenylenedione fluorene

Participants

Reaction Steps

A mixture of compound 9 (150.0 mg, 0.173 mmol), 2,2′-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (131.0 mg, 0.173 mmol), and Aliquat 336 (0.02 g) was degassed 3 times with N2 before 3.0 mL of dry toluene was added. Tetrakis(triphenylphosphine)palladium (10 mg, 0.005 mmol) in an aqueous sodium carbonate solution (0.6 mL, 2M, deaerated for 2 hours) was added under N2. The mixture was stirred vigorously and heated at the refluxing temperature for 2 days. The highly viscous reaction mixture was poured into a boiling methanol (30 mL) to precipitate an orange polymer. The polymer was collected by filtration and washed with acetone, methanol, water, and dried under vacuum at 60° C. overnight. The polymer was dissolved in THF (170 mg in 9 mL of THF) and reprecipitated with 40 mL of acetone twice to give 140 mg of TPDKF as an orange polymer (45%); and Elemental analysis: C, 87.30; H, 9.57; O, 2.58.

Provenance & Evidence