Direct C–H arylation vs Stille polymerization: Rational design, synthesis, and systematic examinations of π-conjugated polymers for organic solar cells

Advancing Integration of Direct C–H Arylation-Derived Star-Shaped Oligomers as Second Acceptors for Ternary Organic Solar Cells

“…Till now, the two most common approaches for creating π-functional materials with a sp 2 C–C skeleton are the Stille and Suzuki reactions which include organometallic coupling partners. As part of these reactions, the coupling of C–M/C–Br occurs, where M might be either B or Sn. − In order to create reliable, economical, and time-saving ways to produce UNFRAs, it is essential to tackle these reactions to avoid the prefunctionalization of C–M bonds. − Direct C–H arylation (DACH), also known as C–H/C–Br cross-coupling, is becoming more popular as a way to formulate organic semiconductor compounds, − owing to its outstanding benefits, including atom- and step-economy, simplified techniques, low environmental impact, and cost-effectiveness. The importance of DACH in OSC research stems from the fact that it is used in the synthesis of a wide variety of oligomers, including linear and nonlinear ones, as well as star oligomers, and polymeric and molecular materials. − …”

Direct C–H Arylation-Derived Oligomeric Building Blocks Incorporated into Conjugated Polymers for Organic Solar Cell Applications

“…The DACH, which stands for high atom economy and is also called C−H/C−Br cross-coupling, has the potential to replace the Suzuki and Stille cross-coupling between the already established C−M and C−Br bonds (where M = B or Sn) due to its benefits, such as lower synthetic processes and simpler waste releases (i.e., HBr). 45−52 In addition, the products that are synthesized by DACH have the potential to display photochemical characteristics that are substantially identical 52 to or even superior to those of Stille products, owing to the avoidance of tin residues in the DACH-derived polymers. 53 In this study, we present an approach for investigating the impact of monomer conjugation lengths on polymer properties: we synthesized the oligomeric precursors BDD 2 , BDD 3 , and BDD 4 (Scheme 1) through a one-pot process via the atom-economical DACH reaction.…”