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Synfacts 2015; 11(1): 0034
DOI: 10.1055/s-0034-1379663
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Phosgene as Key Reagent for Trifunctionalization of BODIPY Dyes

Contributor(s):
Timothy M. Swager
,
Sibo Lin
Wang H, Fronczek FR, Vincente MG. H, Smith KM * Louisiana State University, Baton Rouge, USA
Functionalization of 3,5,8-Trichlorinated BODIPY Dyes.

J. Org. Chem. 2014;
79: 10342-10352
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Further Information

Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

fluorophores - Stille coupling - dyes

Significance

The functionalization of BODIPY fluorescent dyes allows the tuning of their photophysical, hydrophobic, and charge-transfer properties. Smith and co-workers utilize phosgene to access a 3,5,8-trichlorinated BODIPY. Exploiting the higher reactivity of the vinylic chloride in Stille couplings, regioselectively functionalized BODIPY dyes are synthesized.


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Comment

Starting from a trichlorinated BODIPY and performing mixed Stille couplings with only four different organotin reagents, 14 new BODIPY dyes are reported in this paper. Photophysical properties are tunable via substitution at the 3-, 5-, and 8-positions. A plethora of regioselectively functionalized BODIPY dyes should be accessible through this strategy.


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