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Thieno‐Fused Subporphyrazines: A New Class of Light Harvesters
Author(s) -
Gotfredsen Henrik,
Storm Freja Eilsø,
Muñoz Alberto Viñas,
Santella Marco,
Kadziola Anders,
Hammerich Ole,
Mikkelsen Kurt V.,
Nielsen Mogens Brøndsted
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201704551
Subject(s) - isoindole , chromophore , absorption (acoustics) , photochemistry , pyrrole , homo/lumo , buckminsterfullerene , chemistry , boron , materials science , stereochemistry , organic chemistry , fullerene , molecule , composite material
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 chromophores attractive candidates for light‐harvesting applications.