title: Regioselective Nucleophilic Functionalization of Antiaromatic Nickel(II) Norcorroles.
abstract: Treatment of antiaromatic nickel(II) norcorrole with potassium cyanide provided nickel(II) 3-cyanonorcorrole with perfect regioselectivity without the help of a catalyst. The reaction of the nickel(II) norcorrole with phenol or thiophenol in the presence of a base also yielded substitution products. The antiaromatic 16π conjugation system in the norcorrole core was preserved in the functionalized products. Introduction of phenylthio groups significantly decreased the HOMO-LUMO gap and enhanced the near IR absorption property.
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Aichi, 464-8603 (Japan).
authors.forename: Ryo
authors.initials: R
authors.lastname: Nozawa
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Aichi, 464-8603 (Japan).
authors.forename: Keitaro
authors.initials: K
authors.lastname: Yamamoto
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Aichi, 464-8603 (Japan).
authors.forename: Ji-Young
authors.initials: JY
authors.lastname: Shin
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Aichi, 464-8603 (Japan).
authors.forename: Satoru
authors.initials: S
authors.lastname: Hiroto
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Aichi, 464-8603 (Japan). hshino@apchem.nagoya-u.ac.jp.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Shinokubo
keywords: X-ray diffraction; aromaticity; electrophilic substitution; nickel; porphyrinoids