Yellow NIR dye: π-fused bisbenzoBODIPYs with electron-withdrawing groups?

Organic & Biomolecular Chemistry Pub Date: 2013-11-28 DOI: 10.1039/C3OB41996G

Abstract

Bicyclo[2.2.2]octadiene-fused (BCOD-fused) bis(benzoborondipyrromethene)s (bisbenzoBODIPYs) bearing electron-withdrawing groups such as fluorine and cyano groups were prepared either by incorporating tetrafluoroisoindole moieties into BODIPY chromophores or by introducing cyano or ethoxycarbonyl groups at the 3,5-positions. The BCOD-fused bisbenzoBODIPYs were quantitatively converted to the corresponding benzene-fused bisbenzoBODIPYs by a retro-Diels–Alder reaction. The π-fused bisbenzoBODIPYs were found to have intense absorption in the near-infrared region and not to have any strong absorption bands in the visible region. Moreover, the bisbenzoBODIPYs were stable under atmospheric conditions.

Graphical abstract: Yellow NIR dye: π-fused bisbenzoBODIPYs with electron-withdrawing groups
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