Four extensively fluorinated tetraphenylethylenes (TPE) and one extensively fluorinated triphenylethylene have been synthesized using combinations of copper‐catalyzed C−H functionalization reactions and Stille coupling reactions. Surprisingly, in contrast to the parent TPE, these compounds show little to no aggregation‐induced emission (AIE). Instead, photocyclization into fluorinated phenanthrene products occurs. Effects of solvent and oxygen on the yield and selectivity of this photocyclization have been examined.
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Vaidya, Tulaza ; Klimovica, Kristine ; LaPointe, Anne M. ; Keresztes, Ivan ; Lobkovsky, Emil B. ; Daugulis, Olafs ; Coates, Geoffrey W. ( , Journal of the American Chemical Society)