Synthesis of Porphyrinquinone and Doubly‐Fused Diporphyrin Quinone Through Oxidation of Diarylporphyrins Using a Hypervalent Iodine Compound

Treatment of a meso‐diarylporphyrin with PhI(OAc)2 in the presence of BF3 ⋅ OEt2 and propionic acid affords the corresponding porphyrinquinone in a high yield (91%). A novel quinone derived from meso‐meso β–β doubly‐fused diporphyrin was obtained as the sole byproduct (16% yield), which exhibits str...

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Veröffentlicht in:Chemistry, an Asian journal an Asian journal, 2020-10, Vol.15 (19), p.3037-3043
Hauptverfasser: Yamashita, Ken‐ichi, Hirano, Daisuke, Fujimaki, Keisuke, Sugiura, Ken‐ichi
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container_end_page 3043
container_issue 19
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container_title Chemistry, an Asian journal
container_volume 15
creator Yamashita, Ken‐ichi
Hirano, Daisuke
Fujimaki, Keisuke
Sugiura, Ken‐ichi
description Treatment of a meso‐diarylporphyrin with PhI(OAc)2 in the presence of BF3 ⋅ OEt2 and propionic acid affords the corresponding porphyrinquinone in a high yield (91%). A novel quinone derived from meso‐meso β–β doubly‐fused diporphyrin was obtained as the sole byproduct (16% yield), which exhibits strong panchromatic absorption between 300 and 1000 nm. It has a low HOMO‐LUMO gap owing to expanded and low‐symmetry π‐planes. Treatment of meso‐diarylporphyrin with PhI(OAc)2 in the presence of BF3 ⋅ OEt2 and propionic acid affords the corresponding quinone in high yield. A novel quinone derived from meso‐meso β–β doubly‐linked diporphyrin is obtained as the sole byproduct. It exhibits strong panchromatic absorption between 300–1000 nm and has a narrow HOMO‐LUMO gap.
doi_str_mv 10.1002/asia.202000781
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source Wiley Online Library Journals Frontfile Complete
subjects Chemistry
Iodine compounds
Molecular orbitals
Oxidation
Panchromatic absorption
Porphyrinoids
Propionic acid
Quinones
Tautomerism
title Synthesis of Porphyrinquinone and Doubly‐Fused Diporphyrin Quinone Through Oxidation of Diarylporphyrins Using a Hypervalent Iodine Compound
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