Specific bromination of fluorinated oligophenylenes, towards cyclo-para- and cyclo-meta-phenylenes

Abstract

This study investigates the synthesis of two distinct classes of macrocycles: non-fluorinated cyclo-para-phenylenes (CPPs) and fluorinated cyclo-meta-phenylenes (CMPSs). On-Surface Synthesis (CPPs): We synthesized quasi-planar, π-extended CPPs on Au(111). Characterization via STM/STS and DFT. Solution-Phase Synthesis (CMPs): We developed a modular route using selective ironmediated bromination to create fluorinated oligophenylene scaffolds. These precursors undergo nickel-mediated Yamamoto coupling to form fluorinated CMPsThis dualmethodology framework explores how curvature, fluorination, and electronic confinement interact within strained benzenoid architectures.