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A<jats:sub>2</jats:sub>B<jats:sub>6</jats:sub>‐type [36]octaphyrins were prepared by the cross condensation of the tetrapyrromethane with aryl aldehydes in moderate yields. A<jats:sub>2</jats:sub>B<jats:sub>6</jats:sub>‐type [36]octaphyrins bearing 2,4,6‐trifluorophenyl, 2,6‐dichlorophenyl, and phenyl substituents underwent Cu<jats:sup>II</jats:sup>‐metalation‐induced fragmentation to give two molecules of AB<jats:sub>3</jats:sub>‐type Cu<jats:sup>II</jats:sup> porphyrins. A<jats:sub>2</jats:sub>B<jats:sub>6</jats:sub>‐type [36]octaphyrin bearing 3‐thienyl substituents underwent thermal <jats:italic>N</jats:italic>‐thienyl fusion reactions to provide a modestly aromatic [38]octaphyrin, which, upon treatment with MnO<jats:sub>2</jats:sub>, underwent further <jats:italic>N</jats:italic>‐thienyl fusion and subsequent oxidation to give a nonaromatic doubly <jats:italic>N</jats:italic>‐thienyl fused [36]octaphyrin.</jats:p>"}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1380004229944648453","@type":"Researcher","foaf:name":[{"@value":"Hirotaka 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