The direct arylation polycondensation of 1,2,4,5-tetrafluorobenzene was achieved by using a low cost precatalyst, palladium on carbon (Pd/C). The reaction efficiency of the polycondensation was improved by choice of appropriate carboxylate additive, phosphine ligand and solvent. The Pd/C-catalyzed direct arylation polycondensation of 1,2,4,5-tetrafluorobenzene with 2,7-dibromo-9,9-dioctylfluorene was carried out using
N,
N-dimethylacetoamide as a solvent in the presence of 1-adamantane carboxylic acid as an additive to give the alternating copolymer, poly[(2,3,5,6-tetrafluorophenyl-1,4-ene)-
alt-(9,9-dioctylfluorene-2,7-diyl)] with a high molecular weight (
Mn = 19000) in good yield. The same polycondensation using toluene as a solvent also afforded the polymer with a high molecular weight (
Mn = 17000) in good yield when pivalic acid was used instead of 1-adamantane carboxylic acid. The characterization of the polymer was performed by both
1H and
19F NMR measurements.
抄録全体を表示