Switching of polymerization activity of cinnamoyl-α-cyclodextrin

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

Switching of polymerization activity of cinnamoyl-α-cyclodextrin†

Motofumi Osaki,^a Yoshinori Takashima,^a Hiroyasu Yamaguchi^a and Akira Harada*^a

Author affiliations

* Corresponding authors

^a Department of Macromolecular Science, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka, Osaka, Japan
E-mail: harada@chem.sci.osaka-u.ac.jp
Fax: +81-6-6850-5445
Tel: +81-6-6850-5445

Abstract

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.

Download options Please wait...

Supplementary files

Article information

DOI: https://doi.org/10.1039/B818241H
Article type: Paper
Submitted: 15 Oct 2008
Accepted: 09 Jan 2009
First published: 04 Mar 2009

Download Citation

Org. Biomol. Chem., 2009,7, 1646-1651

Permissions

Request permissions