Issue 26, 2016
From the journal:

Organic & Biomolecular Chemistry

Synthesis and regioselective functionalization of perhalogenated BODIPYs†

Ning Zhao,a   Sunting Xuan,a   Brandon Byrd,a   Frank R. Fronczek,a   Kevin M. Smitha  and  M. Graça H. Vicente*a  

* Corresponding authors

a Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA
E-mail: vicente@lsu.edu

Abstract

Three perhalogenated BODIPYs (1b–3b), bearing chloro and bromo groups at all carbon positions, were synthesized and characterized. The reactivity of BODIPY 3b was investigated under Stille cross-coupling reactions, and single crystal X-ray analysis was used to confirm the regioselectivity of the reactions. Further substitution at the boron atom produced nona-functionalized BODIPYs 7a,b, which show 676 and 739 nm emissions with 91 and 100 nm Stokes shifts, respectively.

Graphical abstract: Synthesis and regioselective functionalization of perhalogenated BODIPYs

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Article information

DOI
https://doi.org/10.1039/C6OB00935B
Article type
Communication
Submitted
29 Apr 2016
Accepted
19 May 2016
First published
25 May 2016

Org. Biomol. Chem., 2016,14, 6184-6188

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Synthesis and regioselective functionalization of perhalogenated BODIPYs

N. Zhao, S. Xuan, B. Byrd, F. R. Fronczek, K. M. Smith and M. G. H. Vicente, Org. Biomol. Chem., 2016, 14, 6184 DOI: 10.1039/C6OB00935B

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