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 °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 fluorescence in the film state, which was also evaluated for use as an emitting material in organic light-emitting diodes. [Display omitted] • One-pot two-step cross-dehydrogenative-coupling polycondensation is demonstrated. • The sequential one-pot two-step reaction effectively suppressed undesired homo-coupling defects. • The regioregular polymer exhibits high crystallinity and strong fluorescence. [ABSTRACT FROM AUTHOR]