First photosensitized enantiodifferentiating isomerization by optically active sensitizer immobilized in zeolite supercages

Wada, Takehiko; Shikimi, Masayuki; Inoue, Yoshihisa; Lem, George; Turro, Nicholas J.

Enantiodifferentiating photoisomerization of (Z)-cyclooctene sensitized by (R)- or (S)-1-methylheptyl benzoate immobilized in zeolite supercages afforded the respective enantiomer pair, (—)- and (+)-(E)-isomer (1E) in 5% enantiomeric excess, whilst racemic 1E was obtained upon homogeneous-phase photosensitization with the same antipodal sensitizer pair, thus demonstrating for the first time that chirally modified zeolites not only serve as supramolecular photosensitizing media but also enhance the original enantiodifferentiating ability of chiral photosensitizer.


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Chemical Communications

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July 23, 2010