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A cascade strategy for vinyl chloride-substituted BODIPYs with tunable photophysical properties
Fan Lv1,2, Xing Guo1, Shuangshuang Zhu2
1Laboratory of Functional Molecular Solids, Ministry of Education, School of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, China. jiao421@ahnu.edu.cn.
Abstract:
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.
