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A Fully Conjugated Porphyrin-[36]Octaphyrin-Porphyrin Hybrid Tape Exhibiting Möbius Aromaticity.

Akito NakaiTakayuki TanakaAtsuhiro Osuka
Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2022)
Directly meso-meso linked porphyrin-tetrabromo[36]octaphyrin-porphyrin hybrid trimer 10 was successfully synthesized via acid-catalyzed condensation reaction and subsequent oxidation. Zn II -metalation of 10 induced transannular meso-meso bond formation to give Möbius aromatic bis-Zn II octaphyrin 11, which was oxidized by DDQ/Sc(OTf) 3 to provide fully conjugated porphyrin-[36]octaphyrin-porphyrin hybrid tape 12 as the first example of porphyrin tape exhibiting Möbius aromaticity. Hybrid tape 12 displays significantly red-shifted absorption and small electrochemical HOMO-LUMO gap, indicating the effective conjugation through the whole chromophores.
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