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

Research output: Contribution to journalArticlepeer-review

32 Citations (Scopus)

Abstract

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 α-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.

Original languageEnglish
Pages (from-to)1305-1311
Number of pages7
JournalBeilstein Journal of Organic Chemistry
Volume8
DOIs
Publication statusPublished - 2012 Aug 16
Externally publishedYes

Keywords

  • 1,3-cyclooctadiene
  • Cyclodextrins
  • Cyclooctene
  • Nanosponge
  • Photochirogenesis
  • Photoisomerization

ASJC Scopus subject areas

  • Organic Chemistry

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