Synthesis and Photocyclization of Fluorinated Tetraphenylethylenes

Five extensively fluorinated tetraphenylethylene (TPE) derivatives have been synthesized using Cu-catalyzed C–H functionalization reactions and Stille couplings. Surprisingly, in contrast to the parent TPE, these compounds show little to no aggregation-induced emission (AIE). Instead, photocyclization into fluorinated phenanthrene products occurs.