TY - JOUR A1 - Wang, Hai Ming A1 - Wenz, Gerhard T1 - Topochemical control of the photodimerization of aromatic compounds by γ-cyclodextrin thioethers in aqueous solution JF - Beilstein Journal of Organic Chemistry PY - 2013/// VL - 9 SP - 1858 EP - 1866 SN - 1860-5397 DO - 10.3762/bjoc.9.217 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.9.217 KW - acenaphthylene KW - anthracene KW - coumarin KW - cyclodextrins KW - photodimerization KW - quantum yield KW - stereoselectivity N2 - The formation of soluble 1:2 complexes within hydrophilic γ-cyclodextrin (γ-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 γ-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. ER -