Redox Switching of Orthoquinone-Containing Aromatic Compounds with Hydrogen and Oxygen Gas

Kazuki Urakawa; Michinori Sumimoto; Mitsuhiro Arisawa; Masaki Matsuda; Hayato Ishikawa

doi:10.1002/anie.201601906

Redox Switching of Orthoquinone-Containing Aromatic Compounds with Hydrogen and Oxygen Gas

Angew Chem Int Ed Engl. 2016 Jun 20;55(26):7432-6. doi: 10.1002/anie.201601906. Epub 2016 May 4.

Authors

Kazuki Urakawa¹, Michinori Sumimoto², Mitsuhiro Arisawa³, Masaki Matsuda⁴, Hayato Ishikawa⁵

Affiliations

¹ 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.
² Division of Computational Chemistry, Graduate School of Science and Engineering, Yamaguchi University, 2-16-1, Tokiwadai, Ube, Yamaguchi, 755-8611, Japan.
³ Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka, 565-0871, Japan.
⁴ 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.
⁵ 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.

PMID: 27145376
DOI: 10.1002/anie.201601906

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.

Keywords: hydroquinones; materials science; quinones; redox switching; twist strain.

Publication types

Research Support, Non-U.S. Gov't