Synthesis of 4,4′-functionalized BODIPYs from dipyrrins
Abstract
© 2015 Elsevier Ltd. A series of 14 symmetric (1a-g) and asymmetric (2a-g) BODIPYs bearing two different substituents at the boron center were synthesized in a one-pot reaction from dipyrrins 1 and 2, respectively, in 14-63% isolated yields. The reaction involves the treatment of dipyrrin with phenylboron dichloride followed by nucleophilic substitution of the chloride group using various nucleophiles, including TBAF, TMSCN, ROH, acetate, and alkoxides. The reactions are completed within 2 h at room temperature. The spectroscopic and 11B NMR properties of the new BODIPYs were investigated and three crystal structures are presented.
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