An efficient and transition-metal-free method for the synthesis of unprecedented vinyl chloride-substituted BODIPYs has been developed through tandem Friedel-Crafts, enolization and chlorination reactions. This transformation offers high regioselectivity and stereoselectivity, enabling the synthesis of a variety of β-vinyl chloride-β'-acyl- and β,β'-divinyl chloride-substituted BODIPYs in a one-pot reaction at room temperature. Further functionalization gave a β,β'-divinyl chloride-substituted BODIPY with triphenyl phosphonium moieties, which showed favorable two-photon mitochondrion-targeting imaging capacity in living cells with intense deep-red fluorescence.

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