title: Redox-Switchable 20π-, 19π-, and 18π-Electron 5,10,15,20-Tetraaryl-5,15-diazaporphyrinoid Nickel(II) Complexes.
abstract: The first examples of air-stable 20π-electron 5,10,15,20-tetraaryl-5,15-diaza-5,15-dihydroporphyrins, their 18π-electron dications, and the 19π-electron radical cation were prepared through metal-templated annulation of nickel(II) bis(5-arylamino-3-chloro-8-mesityldipyrrin) complexes followed by oxidation. The neutral 20π-electron derivatives are antiaromatic and the cationic 18π-electron derivatives are aromatic in terms of the magnetic criterion of aromaticity. The meso N atoms in these diazaporphyrinoids give rise to characteristic redox and optical properties for the compounds that are not typical of isoelectronic 5,10,15,20-tetraarylporphyrins.
authors.affiliation: Department of Chemistry, Faculty of Science, Niigata University, Nishi-ku, Niigata, 950-2181, Japan.
authors.forename: Takaharu
authors.initials: T
authors.lastname: Satoh
authors.affiliation: Department of Chemistry, College of Science, Rikkyo University, Toshima-ku, Tokyo, 171-8501, Japan.
authors.forename: Mao
authors.initials: M
authors.lastname: Minoura
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyushu University, Nishi-ku, Fukuoka, 819-0395, Japan.
authors.forename: Haruyuki
authors.initials: H
authors.lastname: Nakano
authors.affiliation: Center for Instrumental Analysis, Institute for Research Promotion, Niigata University, Nishi-ku, Niigata, 950-2181, Japan.
authors.forename: Ko
authors.initials: K
authors.lastname: Furukawa
authors.affiliation: Department of Chemistry, Faculty of Science, Niigata University, Nishi-ku, Niigata, 950-2181, Japan. matano@chem.sc.niigata-u.ac.jp.
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Matano
keywords: annulenes; aromaticity; heterocyclic compounds; porphyrinoids; redox chemistry