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- Title
Selective Formation of Helical Tetrapyrrin‐Fused Porphyrins by Oxidation of β‐to‐β Linked meso‐Aminoporphyrin Dimers.
- Authors
Fujimoto, Keisuke; Shimizu, Daiki; Mori, Tadashi; Li, Yuanyuan; Zhou, Mingbo; Song, Jianxin; Osuka, Atsuhiro
- Abstract
Oxidation of β‐to‐β directly linked and sulfur‐bridged meso‐amino NiII‐porphyrin dimers with PbO2 gave helical tetrapyrrin (biliverdin analogue)‐fused NiII‐porphyrins. These ring cleaving reactions differ markedly from the previously reported oxidation of a β–β linked NiII‐porphyrin dimer carrying one amino group, which gave an azepine‐fused porphyrin dimer. The tetrapyrrin‐fused NiII‐porphyrins display intense NIR absorption bands at 1200–1400 nm and reversible redox processes because of the highly π‐conjugated networks and rigid structures. These tetrapyrrin‐fused NiII‐porphyrins were separated to stable enantiomers, which showed clear Cotton effects in their CD spectra with Δϵ of 102 order. Oxidation of β‐to‐β directly linked and sulfur‐bridged meso‐amino NiII‐porphyrin dimers gave helical tetrapyrrin‐fused NiII‐porphyrins, which displayed intense NIR absorption bands and reversible redox processes because of their highly π‐conjugated networks. These porphyrins were separated into enantiomers, which showed clear Cotton effects in their CD spectra.
- Subjects
OXIDATION; PORPHYRINS; CHEMICAL reactions; ENANTIOMERS; AZEPINES
- Publication
Chemistry - A European Journal, 2019, Vol 25, Issue 7, p1711
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201805659