Methanol → 9,9-Dioctyl-9H-fluorene

Participants

Reaction Conditions

Reaction Steps

To a mixture of 9,9-di-n-octylfluorene-2,7-di(ethyleneboronate) (monomer (1)), R=n-octyl, 15.8 g, 29.49 mmol), 2,7-dibromo-9,9-di-n-octylfluorene (16.18 g, 29.49 mmol, (monomer (2)), R=n-octyl) in toluene (130 mL) under nitrogen is added Aliquat® 336 (1.5 g, 3.7 mmol), tetrakis(triphenylphosphine)palladium (0.18 g, 0.15 mmol), and 2M aqueous sodium carbonate (50 mL, 100 mmol). The mixture is stirred vigorously and heated at gentle reflux for 2 hours when a viscous reaction mixture is observed. An additional 50 mL of toluene is added and the reaction continued for another 15 hours. Sixty mL of toluene is then added to the very viscous reaction mixture and the heating and stirring are continued for 9 more hours. At the end of this period, the polymer is capped by adding 2 g of phenyl ethyleneboronate followed by heating for 15 hours, and one gram of bromobenzene followed by heating for 5 hours. The reaction mixture is cooled to about 60° C. and is added slowly to a stirred solution of 3 L of methanol and 300 mL of deionized water. The fibrous polymer is collected by filtration and is washed successively with methanol (500 mL), deionized water (200mL), and methanol (800 mL), and then dried in vacuum at 60° C. for 10 hours. The polymer weighed 23 g (100% yield). The inherent viscosity of the polymer is 1.50 dL/g. Molecular weight measurement by gel permeation chromatography shows a Mw of 148,00 g/mole, Mn of 47,980 g/mole relative to polystyrene standards. The spectral characteristics of the polymer are consistent with the structure: ##STR7##

Provenance & Evidence