H2SO4-catalyzed one-step synthesis of β,β′-carbon-bridged bisBODIPYs from BODIPYs and aldehydes

Abstract

An H₂SO₄-promoted condensation reaction between BODIPYs and aldehydes has been established, enabling a straightforward and versatile approach for the highly regioselectivity synthesis of β,β′-carbon-bridged bisBODIPYs. This one-step method efficiently facilitates the condensation of a range of aldehydes, including aromatic, heteroaromatic, and aliphatic derivatives to deliver the corresponding target products. Importantly, by eliminating multi-step procedures and circumventing the manipulation of labile intermediates, this approach significantly streamlines the synthetic process. Furthermore, bisBODIPY 1j exhibits a high singlet oxygen quantum yield of 0.81 in toluene, demonstrating its potential as a highly efficient photosensitizer for promising applications in photodynamic therapy and photocatalytic organic transformations.