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

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

Research output: Contribution to journal › Article › peer-review

48 Scopus citations

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.

Original language	English
Pages (from-to)	8703-8707
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	141
Issue number	22
Early online date	Jun 5 2019
DOIs	https://doi.org/10.1021/jacs.9b03235
State	Published - Jun 5 2019
Externally published	Yes

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title = "Highly Luminescent Heavier Main Group Analogues of Boron-Dipyrromethene",

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 (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.",

author = "Wang Wan and Silva, \{Mayura S.\} and McMillen, \{Colin D.\} and Creager, \{Stephen E.\} and Smith, \{Rhett C.\}",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

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T1 - Highly Luminescent Heavier Main Group Analogues of Boron-Dipyrromethene

AU - Wan, Wang

AU - Silva, Mayura S.

AU - McMillen, Colin D.

AU - Creager, Stephen E.

AU - Smith, Rhett C.

PY - 2019/6/5

Y1 - 2019/6/5

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85066859517

U2 - 10.1021/jacs.9b03235

DO - 10.1021/jacs.9b03235

M3 - Article

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SN - 0002-7863

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EP - 8707

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 22

ER -

Highly Luminescent Heavier Main Group Analogues of Boron-Dipyrromethene

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