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Issue 7, 2016
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Synthesis and spectroscopic properties of β,β′-dibenzo-3,5,8-triaryl-BODIPYs

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Abstract

A series of β,β′-bicyclo-3,5-diaryl-BODIPYs were synthesized from the corresponding β,β′-bicyclo-3,5-diiodo-BODIPYs (1a,b) via Pd(0)-mediated Suzuki cross-coupling reactions in 82–92% yields. Subsequent aromatization with DDQ afforded the corresponding β,β′-dibenzo-aryl-BODIPYs, which showed red-shifted absorptions and emissions in the near-IR range. The dibenzo-appended BODIPYs showed characteristic 1H-, 13C-, 11B- and 19F-NMR shifts, and nearly planar conformations by X-ray crystallography.

Graphical abstract: Synthesis and spectroscopic properties of β,β′-dibenzo-3,5,8-triaryl-BODIPYs

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Article information


Submitted
24 Nov 2015
Accepted
08 Feb 2016
First published
08 Feb 2016

New J. Chem., 2016,40, 5740-5751
Article type
Paper

Synthesis and spectroscopic properties of β,β′-dibenzo-3,5,8-triaryl-BODIPYs

Q. Meng, F. R. Fronczek and M. G. H. Vicente, New J. Chem., 2016, 40, 5740
DOI: 10.1039/C5NJ03324A

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