Synthesis and regioselective functionalization of perhalogenated BODIPYs

Three perhalogenated BODIPYs ( 1b-3b ), bearing chloro and bromo groups at all carbon positions, were synthesized and characterized. The reactivity of BODIPY 3b was investigated under Stille cross-coupling reactions, and single crystal X-ray analysis was used to confirm the regioselectivity of the reactions. Further substitution at the boron atom produced nona-functionalized BODIPYs 7a,b , which show 676 and 739 nm emissions with 91 and 100 nm Stokes shifts, respectively. We report the synthesis of perhalogenated BODIPYs and investigate the regioselective functionalization of a perhalogenated BODIPY using Pd(0)-catalyzed Stille cross-coupling reactions. Further reaction at the boron atom produces nona-functionalized BODIPYs.