Boron templated synthesis of a BODIPY analogue from a phthalocyanine precursor

Abstract

The synthesis of aza(dibenzopyrro)methenes (ADBM) using aryl boron compounds as templates is described. The resultant half phthalocyanine BPh₂ compounds (1–3) are structurally related to the BODIPY class of fluorophores and were isolated with terminal imine, terminal oxo, or mixed imine-oxo heteroatom positions. Compounds 1–3 were investigated for their absorption/emission properties, and large stokes shifts of ∼50 nm were observed for fluorescence emission. The electronic structures of 1–3 were probed by TD/DFT methods.