title: Redox Switching of Orthoquinone-Containing Aromatic Compounds with Hydrogen and Oxygen Gas.
abstract: Unique redox switching of orthoquinone-containing pentacyclic aromatic compounds with molecular hydrogen and oxygen in the presence of a palladium nanoparticle catalyst (SAPd) is disclosed. These molecules were predicted by in silico screening before synthesis. Efficient protocols for the synthesis of orthoquinone-containing aromatic compounds by palladium-mediated homocoupling and the benzoin condensation reaction were developed. Clear switching between orthoquinone and aromatic hydroquinone compounds was observed on the basis of their photoluminescence properties. Furthermore, the twist strain of the orthoquinone moiety could induce dramatic changes in color and emission.
authors.affiliation: Division of Organic Chemistry, Department of Chemistry, Graduate School of Science and Technology, Kumamoto University, 2-39-1, Kurokami, Chuo-ku, Kumamoto, 860-8555, Japan.
authors.forename: Kazuki
authors.initials: K
authors.lastname: Urakawa
authors.affiliation: Division of Computational Chemistry, Graduate School of Science and Engineering, Yamaguchi University, 2-16-1, Tokiwadai, Ube, Yamaguchi, 755-8611, Japan.
authors.forename: Michinori
authors.initials: M
authors.lastname: Sumimoto
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka, 565-0871, Japan.
authors.forename: Mitsuhiro
authors.initials: M
authors.lastname: Arisawa
authors.affiliation: Division of Physical Chemistry, Department of Chemistry, Graduate School of Science and Technology, Kumamoto University, 2-39-1, Kurokami, Chuo-ku, Kumamoto, 860-8555, Japan. masaki@sci.kumamoto-u.ac.jp.
authors.forename: Masaki
authors.initials: M
authors.lastname: Matsuda
authors.affiliation: Division of Organic Chemistry, Department of Chemistry, Graduate School of Science and Technology, Kumamoto University, 2-39-1, Kurokami, Chuo-ku, Kumamoto, 860-8555, Japan. ishikawa@sci.kumamoto-u.ac.jp.
authors.forename: Hayato
authors.identifier: 0000-0002-3884-2583
authors.initials: H
authors.lastname: Ishikawa
keywords: hydroquinones; materials science; quinones; redox switching; twist strain