Synthesis of conjugated ladder-type oligomers and polymer via Suzuki coupling and Knoevenagel condensation domino reaction

The facile and efficient synthesis of extended ladder-type benzo[ k ]tetraphene-derived (BTp) oligomers and polymers without defects has long been a challenge. In this paper, we combine Suzuki coupling and Knoevenagel condensation reactions to prepare BTp-based oligomers and a polymer. In this process, the Suzuki coupling and Knoevenagel condensation proceed sequentially under standard Suzuki coupling conditions. Notably, the Knoevenagel condensation does not occur prior to the Suzuki coupling. To demonstrate the applicability of the domino reaction, a series of ribbon-shaped conjugated oligomers were synthesized and fully characterized by 1 H NMR, 13 C NMR, and HRMS. The facile reaction process and high yields demonstrate that the domino reaction is an efficient method for synthesizing conjugated ladder-type polymers.