Beilstein Journal of Organic Chemistry (Aug 2012)

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

  • Wenting Liang,
  • Cheng Yang,
  • Masaki Nishijima,
  • Gaku Fukuhara,
  • Tadashi Mori,
  • Andrea Mele,
  • Franca Castiglione,
  • Fabrizio Caldera,
  • Francesco Trotta,
  • Yoshihisa Inoue

DOI
https://doi.org/10.3762/bjoc.8.149
Journal volume & issue
Vol. 8, no. 1
pp. 1305 – 1311

Abstract

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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 of the nanosponges incorporating β- or γ-cyclodextrin was significantly different from that reported for the conventional sensitizer-appended monomeric cyclodextrins, affording chiral (E)-cyclooctene and (E,Z)-cyclooctadiene in enantiomeric excesses critically dependent on the solution pH and solvent composition employed, revealing the active roles of chiral void spaces of CDNS in the photochirogenic reaction.

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