meso–meso‐Linked Diarylamine‐Fused Porphyrin Dimers |
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Authors: | Norihito Fukui Prof?Dr Hideki Yorimitsu Prof?Dr Atsuhiro Osuka |
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Institution: | Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, Japan |
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Abstract: | A meso–meso‐linked diphenylamine‐fused porphyrin dimer and its methoxy‐substituted analogue were synthesized from a meso–meso‐linked porphyrin dimer by a reaction sequence involving Ir‐catalyzed β‐selective borylation, iodination, meso‐chlorination, and SNAr reactions with diarylamines followed by electron‐transfer‐mediated intramolecular double C?H/C?I coupling. While these dimers commonly display characteristic split Soret bands and small oxidation potentials, they produced different products upon oxidation with tris(4‐bromophenyl)aminium hexachloroantimonate. Namely, the diphenylamine‐fused porphyrin dimer was converted into a dicationic closed‐shell quinonoidal dimer, while the methoxy‐substituted dimer gave a meso–meso, β‐β doubly linked porphyrin dimer. |
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Keywords: | dimers fusion reactions oxidation porphyrins UV spectroscopy |
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