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Pure Appl. Chem., 2011, Vol. 83, No. 4, pp. 769-778

Published online 2011-02-23

Supramolecular complexation and photocyclodimerization of methyl 3‑methoxy‑2‑naphthoate with modified γ‑cyclodextrins

Wenting Liang1, Hui-Hui Zhang2, Jing-Jing Wang2, Yuan Peng3, Bin Chen2, Cheng Yang1*, Chen-Ho Tung2, Li-Zhu Wu2*, Gaku Fukuhara1, Tadashi Mori1 and Yoshihisa Inoue1*

1 PRESTO, JST and Department of Chemistry, Osaka University, Yamada-oka, Suita 565-0871, Japan
2 Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry & Graduate University, The Chinese Academy of Sciences, Beijing 100190 China
3 Chengdu Environment Monitoring Center, Chengdu 610071, China

Abstract: A series of modified γ-cyclodextrins (CDs) were prepared as chiral host for catalyzing the enantiodifferentiating photocyclodimerization of methyl 3-methoxy-2-naphthoate (NA). The complexation behavior of NA with modified γ-CDs was studied by UV–vis, fluorescence, and circular dichroism spectroscopies. All of the modified γ-CDs formed stable 1:2 host–guest complex with NA, and binding affinities for two-step complexation critically depended on the structure of modified γ-CDs. The enantioselectivity of NA photocyclodimerization was also significantly affected by the modification of γ-CD. The secondary rim-modification considerably reduced the enantioselectivity, for which the interrupted hydrogen-bonding network, leading to a flexible CD skeleton, is most probably responsible.