Supramolecular photochirogenesis in sensitizing chiral nanopore: Enantiodifferentiating photoisomerization of (Z)-cyclooctene included and sensitized by POST-1

Abstract

By using homochiral mesoporous POST-1 (Scheme 1) as an inherently chiral sensitizing host, supramolecular enantiodifferentiating photoisomerizations of (Z)-cyclooctene (1Z) were performed for the first time to examine the sensitizing ability of the chiral nanopores, walls of which are decorated with pyridine chromophore. The homochiral nanopores of POST-1 crystals were demonstrated to function as an effective chiral-sensitizing cavity to give the optically active (E)-isomer 1E in up to 5% enantiomeric excess (ee), thus expanding the scope of porous material-mediated chirogenesis to both ground and excited electronic states. Chirality 17:S19-S23, 2005. (c) 2005 Wiley-Liss, Inc.