title: Iridium-catalyzed direct tetraborylation of perylene bisimides.
abstract: Treatment of perylene bisimides (PBIs) with bis(pinacolato)diboron in the presence of an iridium catalyst provides tetraborylated PBIs at 2,5,8,11-positions in good yields with perfect regioselectivity. The planar structure of the perylene core has been confirmed by X-ray diffraction analysis. Oxidation of tetraborylated PBI with hydroxylamine hydrochloride affords tetrahydroxy PBI in excellent yield, which exhibits a substantially blue-shifted absorption spectrum due to an intramolecular hydrogenbonding interaction between carbonyl and hydroxy groups.
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya, Japan.
authors.forename: Takuro
authors.initials: T
authors.lastname: Teraoka
authors.forename: Satoru
authors.initials: S
authors.lastname: Hiroto
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Shinokubo