Highly Luminescent Heavier Main Group Analogues of Boron-Dipyrromethene

Wang Wan; Mayura S Silva; Colin D McMillen; Stephen E Creager; Rhett C Smith

doi:10.1021/jacs.9b03235

Highly Luminescent Heavier Main Group Analogues of Boron-Dipyrromethene

J Am Chem Soc. 2019 Jun 5;141(22):8703-8707. doi: 10.1021/jacs.9b03235. Epub 2019 May 23.

Authors

Wang Wan¹, Mayura S Silva¹, Colin D McMillen¹, Stephen E Creager^{1

2}, Rhett C Smith^{1

2}

Affiliations

¹ Department of Chemistry , Clemson University , Clemson , South Carolina 29634 , United States.
² Center for Optical Materials Science and Engineering Technology, Clemson University , Anderson , South Carolina 29625 , United States.

PMID: 31120244
DOI: 10.1021/jacs.9b03235

Abstract

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 (λ_em = 505 nm, Φ_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.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.