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...

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Bibliographic Details
Published in:Synthetic metals 2023-03, Vol.293, p.117279, Article 117279
Main Authors: Onda, Naoki, Sato, Ryota, Kuwabara, Junpei, Yasuda, Takeshi, Kanbara, Takaki
Format: Article
Language:English
Subjects:
Conjugated polymers
Cross-dehydrogenative-coupling reaction
Emitting materials
Pd/Ag dual-catalyst
Polycondensation
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Summary: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.
ISSN:0379-6779
1879-3290
DOI:10.1016/j.synthmet.2023.117279