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Issue 8, 2009
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Switching of polymerization activity of cinnamoyl-α-cyclodextrin

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Cinnamoyl α-cyclodextrin (α-CD) has been found to initiate polymerization of δ-valerolactone (δ-VL) to give a polymer in high yield. By the presence of the cinnamoyl group, hydrogen bond was formed between the carbonyl oxygen of δ-VL and the hydroxyl group of CD to activate the monomer, which was observed by FT-IR measurements. However, the cinnamoyl group at the C3- and C6-positions of α-CD did not affect the polymerization ability. Only that of the C2-position showed high polymerization activity. The polymerization activity could be switched by the photoisomerization of the cinnamoyl group attached to the rim of α-CD. Specific monomer recognition and polymerization in the active site of the α-CD cavity was changed by the photoisomerization.

Graphical abstract: Switching of polymerization activity of cinnamoyl-α-cyclodextrin

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Article information

15 Oct 2008
09 Jan 2009
First published
04 Mar 2009

Org. Biomol. Chem., 2009,7, 1646-1651
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Switching of polymerization activity of cinnamoyl-α-cyclodextrin

M. Osaki, Y. Takashima, H. Yamaguchi and A. Harada, Org. Biomol. Chem., 2009, 7, 1646
DOI: 10.1039/B818241H

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