Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 7, Issue 4, Pages 826-829Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201101005
Keywords
electron-deficient compounds; host-guest systems; photooxidation; self-assembly; triquinacene
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Funding
- CREST of the Japan Science and Technology Agency (JST)
- MEXT, Japan
- Grants-in-Aid for Scientific Research [23750057] Funding Source: KAKEN
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Triquinacene is a concave tricyclic hydrocarbon with diverse photoreactivity. In the cavity of an electron-accepting molecular host, triquinacene was specifically photooxidized at the peripheral allylic position into an alcohol, 1-hydroxytriquinacene, via guest-to-host electron transfer. The unusual reactivity stems from the extremely electron-deficient triazine panel ligand of the host cage, which allows the cage to function as a good electron acceptor. Thus, self-assembled coordination cages can serve not only as molecular-sized reaction vessels but also function electronically as redox media. Dissolved molecular oxygen is indispensable for the photoreaction and immediately traps a photogenerated radical.
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