Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 26, Pages 7432-7436Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201601906
Keywords
hydroquinones; materials science; quinones; redox switching; twist strain
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Funding
- JSPS [15K13647]
- MEXT [2304, 26105750]
- Grants-in-Aid for Scientific Research [15KT0063, 26105750, 16K05752, 25410097, 16H01026, 15K13647] Funding Source: KAKEN
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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.
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