Jump to main content
Jump to site search

Issue 34, 2012
Previous Article Next Article

π-Fused bis-BODIPY as a candidate for NIR dyes

Author affiliations


Benzene-fused bis-(borondipyrromethene)s (bis-BODIPYs) were synthesized by retro-Diels–Alder reaction of the corresponding bicyclo[2.2.2]octadiene-fused (BCOD-fused) bis-BODIPYs, which were, in turn, prepared from 4,8-ethano-4,8-dihydropyrrolo[3,4-f]isoindole derivatives. The π-fused bis-BODIPY chromophores were designed to show intensive absorption and strong fluorescence in the near-infrared region and not to have any strong absorption in the visible region. A 6,10-dibora-5a,6a,9a,10a-tetraaza-s-indaceno[2,3-b:6,5-b′]difluorene derivative (syn-bis-benzoBODIPY) obtained by a thermal retro-Diels–Alder reaction of the corresponding BCOD-fused BODIPY dimer has strong absorption and emission bands at 775 and 781 nm, respectively. The absolute quantum yield is 0.36. The absorption is more than 5.0 times stronger than other absorptions observed in the visible region. In the case of 6,15-dibora-5a,6a,14a,15a-tetraaza-s-indaceno[2,3-b:6,7-b′]difluorene derivatives (anti-bis-benzoBODIPY), the absorption and emission maxima exceed 840 nm.

Graphical abstract: π-Fused bis-BODIPY as a candidate for NIR dyes

Back to tab navigation

Supplementary files

Publication details

The article was received on 15 May 2012, accepted on 28 Jun 2012 and first published on 04 Jul 2012

Article type: Paper
DOI: 10.1039/C2OB25930C
Org. Biomol. Chem., 2012,10, 6840-6849

  •   Request permissions

    π-Fused bis-BODIPY as a candidate for NIR dyes

    M. Nakamura, H. Tahara, K. Takahashi, T. Nagata, H. Uoyama, D. Kuzuhara, S. Mori, T. Okujima, H. Yamada and H. Uno, Org. Biomol. Chem., 2012, 10, 6840
    DOI: 10.1039/C2OB25930C

Search articles by author