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Stereoselective Photodimerization of 2-Anthracenecarboxylic Acid Using a Cation-Charged PSMP12-Cyclodextrin Template

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Abstract

Two pyridinium groups were introduced into β-cyclodextrin (β-CD) at the A and E glucose units to make a molecular flask for controlling the stereo-selectivity of photodimerization of 2-anthracenecarboxylic acid. When the photodimerization of 2-anthracenecarboxylic acid was carried out in the presence of bispyridinio-appended β-CD, the relative yield of one of the configurational isomers was increased 1.5-fold compared to the corresponding yield in aqueous solution. The optical yields of the photodimerization reaction products also increased more than 10-fold by the addition of bispyridinio-appended β-CD.

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Ikeda, H., Nihei, T. & Ueno, A. Stereoselective Photodimerization of 2-Anthracenecarboxylic Acid Using a Cation-Charged PSMP12-Cyclodextrin Template. Journal of Inclusion Phenomena 50, 63–66 (2004). https://doi.org/10.1007/s10847-004-8840-x

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  • DOI: https://doi.org/10.1007/s10847-004-8840-x

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