Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 64, Pages 16194-16198Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201704551
Keywords
aromaticity; chromophores; fullerenes; subphthalocyanines; thiophenes
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Funding
- University of Copenhagen
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Boron subphthalocyanines comprised of three isoindole units bridged by aza-linkages are attractive light harvesters on account of their intense low-energy absorptions. Herein, we present a class of related compounds, in which one or two isoindole units are substituted for thieno[3,4-c] pyrrole units - thieno-fused subporphyrazines. Such changes have remarkable consequences for the optical properties, as was revealed by combined experimental and theoretical studies. Thus, we find that the lowest-energy absorptions cover a much broader region with a significantly redshifted end-absorption and without compromising the absorption intensities. Thieno-fused subporphyrazines also underwent more readily oxidation and reduction, indicating an increased HOMO energy and decreased LUMO energy. In addition, they were found to readily co-crystallize with Buckminsterfullerene, C-60. Altogether, these findings render this new class of chromo-phores attractive candidates for light-harvesting applications.
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