Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 18, Pages 6079-6085Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo101255g
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Funding
- JSPS [22350060]
- Grants-in-Aid for Scientific Research [22350060] Funding Source: KAKEN
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The optical properties of 2,6-diacetoxyanthracene 4 encapsulated in the self-assembled boronic ester cavitand capsule 3 in C(6)H(6) are described. Upon excitation at 285 nm, the encapsulated 4 showed strong fluorescence emission as a result of the energy transfer from the excited 3 to the encapsulated 4, while 4 alone in C(6)H(6) exhibited very weak emission. Upon photoirradiation at 365 nm, the encapsulated 4 also showed strong fluorescence emission and remained almost intact, whereas 4 alone in C(6)H(6) gradually underwent photodimerization and photooxygenation to afford photodimers 5 and 5' and 9,10-anthraquinone 6 via 9,10-endoperoxide 7, respectively. Thus, the capsule 3 serves as a photosensitizer for the encapsulated 4 as well as a guard nanocontainer to protect against the photochemical reactions of 4.
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