Issue 9, 2011

Role of entropy in supramolecular photochirogenesis: enantiodifferentiating photoisomerization of cyclooctenes in chiral sensitizer-immobilized MCM-41 cavities

Abstract

To examine the effects of confinement, or low-entropy environments, we employed the mesoporous silicate MCM-41 modified with optically active benzenetetracarboxylates as chiral reaction media to effect the enantiodifferentiating photoisomerization of (Z)-cyclooctene and (Z,Z)-1,5-cyclooctadiene. The ee of the (E)-isomer produced and its temperature dependence behavior in MCM-41 were completely different from those observed in homogeneous solutions. Immobilizing the sensitizer in MCM-41 reduced the contribution of the entropy factor.

Graphical abstract: Role of entropy in supramolecular photochirogenesis: enantiodifferentiating photoisomerization of cyclooctenes in chiral sensitizer-immobilized MCM-41 cavities

Supplementary files

Article information

Article type
Communication
Submitted
03 Mar 2011
Accepted
12 Apr 2011
First published
09 Jun 2011

Photochem. Photobiol. Sci., 2011,10, 1390-1392

Role of entropy in supramolecular photochirogenesis: enantiodifferentiating photoisomerization of cyclooctenes in chiral sensitizer-immobilized MCM-41 cavities

R. Maeda, T. Wada, A. Kusaka, T. Mori, M. Iwamoto and Y. Inoue, Photochem. Photobiol. Sci., 2011, 10, 1390 DOI: 10.1039/C1PP05087G

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