Cyclodextrin nanosponge-sensitized enantiodifferentiating photoisomerization of cyclooctene and 1,3-cyclooctadiene

• DOI: 10.3762/bjoc.8.149
• Publication Date: 2012-08-16T12:04:43Z
• Authors: Wenting Liang; Cheng Yang; Masaki Nishijima; Gaku Fukuhara; Tadashi Mori; Andrea Mele; Franca Castiglione; Fabrizio Caldera; Francesco Trotta; Yoshihisa Inoue
• Keywords: Cyclooctene; 1,5-Cyclooctadiene

Enantiodifferentiating geometrical photoisomerizations of (Z)-cyclooctene and (Z,Z)-1,3-cyclooctadiene were performed by using the pyromellitate-linked cyclodextrin network polymer, termed "cyclodextrin nanosponge (CDNS)", as a supramolecular sensitizing host. The photochirogenic behavior nanosponges incorporating β- or γ-cyclodextrin was significantly different from that reported for conventional sensitizer-appended monomeric cyclodextrins, affording chiral (E)-cyclooctene (E,Z)-cyclooctadiene in enantiomeric excesses critically dependent on solution pH solvent composition employed, revealing active roles void spaces CDNS reaction.