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- Title
A 1,5‐Naphthyridine‐Fused Porphyrin Dimer: Intense NIR Absorption and Facile Redox Interconversion with Its Reduced Congener.
- Authors
Fujimoto, Keisuke; Osuka, Atsuhiro
- Abstract
Abstract: PtII‐catalyzed cyclization of β‐to‐β ethynylene‐bridged <italic>meso</italic>‐amino NiII porphyrin dimer <bold>4</bold> followed by oxidation with PbO2 afforded 1,5‐naphthyridine‐fused porphyrin dimer <bold>5</bold> in good yield. This dimer possesses a redox‐active 1,4‐diazabutadiene linkage that is interconvertible with its reduced 1,2‐diaminoethene linkage upon treatments with NaBH4 or PbO2. The dimer <bold>5</bold> exhibits an intense NIR absorption and a narrow HOMO–LUMO gap with a remarkably low reduction potential mainly due to effective bonding interactions in the LUMO through the 1,4‐diazabutadiene linkage. In contrast, the reduced dimer <bold>7</bold> is fairly electron‐rich with high HOMO energy and shows a relatively large HOMO–LUMO gap compared to that of <bold>5</bold>.
- Subjects
PLATINUM catalysts; NAPHTHYRIDINES; ABSORPTION; OXIDATION-reduction reaction; PORPHYRINS; CHEMICAL yield
- Publication
Chemistry - A European Journal, 2018, Vol 24, Issue 25, p6530
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201800854