Entropy-controlled supramolecular photochirogenesis: Enantiodifferentiating Z-E photoisomerization of cyclooctene included and sensitized by permethylated 6-O-benzoyl-β-cyclodextrin

Gaku Fukuhara; Tadashi Mori; Takehiko Wada; Yoshihisa Inoue

doi:10.1039/b504948b

Entropy-controlled supramolecular photochirogenesis: Enantiodifferentiating Z-E photoisomerization of cyclooctene included and sensitized by permethylated 6-O-benzoyl-β-cyclodextrin

Gaku Fukuhara, Tadashi Mori, Takehiko Wada, Yoshihisa Inoue

IMRAM - Division of Organic- and Biomaterials Research

Research output: Contribution to journal › Article › peer-review

43 Citations (Scopus)

Abstract

In contrast to the photosensitization with a non-methylated analogue, supramolecular photochirogenesis with a novel permethylated mono(6-O-benzoyl)- β-cyclodextrin exhibited a critical dependence of the product's enantiomeric excess upon temperature, and possessed a large differential entropy of activation (-11 J K^-1 mol^-1) for which the flexible host skeleton is likely to be responsible.

Original language	English
Pages (from-to)	4199-4201
Number of pages	3
Journal	Chemical Communications
Issue number	33
DOIs	https://doi.org/10.1039/b504948b
Publication status	Published - 2005 Sept 7

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abstract = "In contrast to the photosensitization with a non-methylated analogue, supramolecular photochirogenesis with a novel permethylated mono(6-O-benzoyl)- β-cyclodextrin exhibited a critical dependence of the product's enantiomeric excess upon temperature, and possessed a large differential entropy of activation (-11 J K-1 mol-1) for which the flexible host skeleton is likely to be responsible.",

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AU - Mori, Tadashi

AU - Wada, Takehiko

AU - Inoue, Yoshihisa

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AB - In contrast to the photosensitization with a non-methylated analogue, supramolecular photochirogenesis with a novel permethylated mono(6-O-benzoyl)- β-cyclodextrin exhibited a critical dependence of the product's enantiomeric excess upon temperature, and possessed a large differential entropy of activation (-11 J K-1 mol-1) for which the flexible host skeleton is likely to be responsible.

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Entropy-controlled supramolecular photochirogenesis: Enantiodifferentiating Z-E photoisomerization of cyclooctene included and sensitized by permethylated 6-O-benzoyl-β-cyclodextrin

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