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 (λem = 505 nm, Φem = 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.