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

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

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.

HYDROGEN; OXYGEN; AROMATIC compounds; CHEMICAL synthesis; OXIDATION-reduction reaction

Angewandte Chemie, 2016, Vol 128, Issue 26, p7558

0044-8249

Academic Journal

10.1002/ange.201601906