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.
A P-C bond-forming reaction has been applied to the convenient preparation of tetraarylphosphonium polyelectrolytes (TPELs) from aryl dihalides and diphenylphosphine. A TPEL having a thermal decomposition temperature of 460 °C that is also stable to heating at 65 °C in 6 M NaOH(aq) for at least 24 h has been prepared by this method.
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