期刊
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
卷 9, 期 -, 页码 1858-1866出版社
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.9.217
关键词
acenaphthylene; anthracene; coumarin; cyclodextrins; photodimerization; quantum yield; stereoselectivity
资金
- Saarland University
- China Scholarship Council
The formation of soluble 1:2 complexes within hydrophilic gamma-cyclodextrin (gamma-CD) thioethers allows to perform photodimerizations of aromatic guests under controlled, homogenous reaction conditions. The quantum yields for unsubstituted anthracene, acenaphthylene, and coumarin complexed in these gamma-CD thioethers were found to be up to 10 times higher than in the non-complexed state. The configuration of the photoproduct reflected the configuration of the dimeric inclusion complex of the guest. Anti-parallel orientation of acenaphthylene within the CD cavity led to the exclusive formation of the anti photo-dimer in quantitative yield. Parallel orientation of coumarin within the complex of a CD thioether led to the formation of the syn head-to-head dimer. The degree of complexation of coumarin could be increased by employing the salting out effect.
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