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International Journal of Polymer Science
Volume 2015, Article ID 419506, 9 pages
http://dx.doi.org/10.1155/2015/419506
Research Article

The Synthesis of the Locating Substitution Derivatives of Chitosan by Click Reaction at the 6-Position of Chitin

1School of Material Science and Engineering, Beijing Institute of Technology, Beijing 100081, China
2School of Chemistry, Beijing Institute of Technology, Beijing 100081, China

Received 28 November 2014; Revised 17 March 2015; Accepted 17 March 2015

Academic Editor: Yulin Deng

Copyright © 2015 Yu Chen et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

A novel method to prepare the macrocyclic compound locating substitution derivatives of chitosan was investigated, by using cyclodextrin as the model of macrocyclic compound. The method combines the advantages of activated 6-OH of chitin and high efficiency of click reaction. Chitin C6-OH p-toluenesulfonate (CTN-6-OTs) was generated and subsequently transferred to chitin C6-N3 via nucleophilic substitution. Afterwards, β-cyclodextrin was immobilized at 6-OH of chitin via click reaction to afford CTN-6-CD. Ultimately, CTS-6-CD was obtained by removing the acetyl group of chitin unit. The structures and properties of these products were characterized by FTIR, TG, and XRD, respectively. It was found that CTN-6-CD synthesized at the optimum conditions has an immobilized loading of  mol/g and that of the corresponding CTS-6-CD, generated by removal of the acetyl group, was  mol/g.