Highly Luminescent Heavier Main Group Analogues of Boron-Dipyrromethene

The preparation and photophysical properties of two heavier main group element analogues of boron-dipyrromethene (BODIPY) chromophores are described. Specifically, we have prepared dipyrrin complexes of dichlorogallate (GADIPY) or phenylphosphenium (PHODIPY) units. Whereas cationic PHODIPY is labile, decomposing to a phosphine over time, GADIPY is readily prepared in good yield as a crystalline solid having moderate air- and water-stability. Crystallographically characterized GADIPY displays intense green photoluminescence (lambda(em) = 505 nm, Phi(em) = 0.91 in toluene). These inaugural heavier main group element analogues of BODIPY offer a glimpse into the potential for elaboration to a panoply of chromophores with diverse photophysical properties.