Iterative Synthesis of Pentacene Derivatives with Continuous Boron–Oxygen Bonds

Iterative syntheses-repeating sequences of the same reactions to construct complex molecules-can facilitate the synthesis of specific classes of small molecules with structural redundancies, including acenes. Despite the prevalence of zigzag edges in the structures of acenes, few examples that effectively manipulate the edge configurations of acenes exist. In this study, the rationally designed iterative synthesis of three pentacene derivatives with continuous boron-oxygen bonds at the zigzag edges is reported. The simple and efficient two-step iteration employed ipso iodination with a trimethylsilyl group as the directing group and Suzuki cross-coupling/condensation reactions. Because of the fundamental role of pentacene derivatives in a broad spectrum of electronic applications, these findings are valuable across a diverse range of chemical and physical disciplines.