Functionalization of an organic fluorophore, boron dipyrromethene (also known as BODIPY) was studied. A series of 4,4'-functionalized BODIPYs were synthesized via nucleophilic substitution from F-BODIPYs and dipyrrins and their spectroscopic properties were investigated. The O-BODIPY compounds were made using three methods: a) nucleophilic addition with sodium alkoxide in methanol, b) Lewis acid mediated and addition of alcohols, c) TMSOTf-activated, followed by addition of alcohols. Seven new 4,4-dialkoxy-BODIPYs were synthesized and six crystal structures were analyzed. In addition, BODIPYs bearing two different substituents on the boron center were synthesized via a one-pot reaction from dipyrrins.

Synthesis of 4,4'-functionalized BODIPYs from F-BODIPYs and dipyrrins

251st National Meeting (2016)

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