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Redox Switching of Orthoquinone‐Containing Aromatic Compounds with Hydrogen and Oxygen Gas
Author(s) -
Urakawa Kazuki,
Sumimoto Michinori,
Arisawa Mitsuhiro,
Matsuda Masaki,
Ishikawa Hayato
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201601906
Subject(s) - hydroquinone , moiety , redox , chemistry , palladium , molecule , oxygen , photochemistry , combinatorial chemistry , catalysis , organic chemistry
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.