One-pot two-step cross-dehydrogenative-coupling polycondensation for synthesis of tetrafluorobenzene-based conjugated polymer

Polycondensation of 1,2,4,5-tetrafluorobenzene (1) with 3,3 '-dihexyl-2,2 '-bithiophene via Pd/Ag dual-catalyzed cross-dehydrogenative coupling was examined. In situ deprotonation-metalation of 1 with Ag salt proceeded smoothly at 25 degrees C, and the subsequent transmetalation with a Pd catalyst provided a cross-coupling product. The sequential one-pot two-step reaction method effectively suppressed undesired homo-coupling defects during polymerization. The obtained highly regioregular polymer had a packing structure and exhibited strong fluo-rescence in the film state, which was also evaluated for use as an emitting material in organic light-emitting diodes.

Automated summary

Polycondensation reaction of 1,2,4,5-tetrafluorobenzene (1) and 3,3'-dihexyl-2,2'-bithiophene was examined via Pd/Ag dual-catalyzed cross-dehydrogenative coupling. In situ deprotonation-metalation of 1 with Ag salt followed by transmetalation with a Pd catalyst successfully produced a cross-coupling product. The one-pot two-step reaction method effectively prevented undesired homo-coupling defects during polymerization. The resulting highly regioregular polymer exhibited a packed structure and strong fluorescence in the film state, showing potential as an emitting material in organic light-emitting diodes.