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Issue 8, 2014
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Yellow NIR dye: π-fused bisbenzoBODIPYs with electron-withdrawing groups

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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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Supplementary files

Article information


Submitted
04 Oct 2013
Accepted
28 Nov 2013
First published
28 Nov 2013

Org. Biomol. Chem., 2014,12, 1309-1317
Article type
Paper
Author version available

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

M. Nakamura, M. Kitatsuka, K. Takahashi, T. Nagata, S. Mori, D. Kuzuhara, T. Okujima, H. Yamada, T. Nakae and H. Uno, Org. Biomol. Chem., 2014, 12, 1309
DOI: 10.1039/C3OB41996G

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