Tetrafluorobenzo-Fused BODIPY: A Platform for Regioselective Synthesis of BODIPY Dye Derivatives

A novel route for the synthesis of
unsymmetrical benzo-fused BODIPYs
is reported using 4,5,6,7-tetrafluoro­iso­indole as a precursor.
The reactivity of the 3,5-dibromo tetrafluorobenzo-fused BODIPY was
investigated under nucleophilic substitution and Pd(0)-catalyzed cross-coupling
reaction conditions. In addition to the 3,5-bromines, one α-fluoro
group on the benzo-fused ring can also be functionalized, and an unusual
homocoupling with formation of a bisBODIPY was observed. This new
class of fluorinated BODIPYs could find various applications in medicine
and materials.