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Synthesis of chitosan 6-OH immobilized cyclodextrin derivates via click chemistry

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Abstract

The synthesis of chitosan 6-OH immobilized cyclodextrin (CTS-6-CD) via click chemistry was investigated. After protecting the 2-NH2 group of chitosan by forming a Schiff base (BCTS) with benzaldehyde, the protected chitosan C6-OH p-toluenesulfonate (BCTS-6-OTs) was generated by treating with p-toluenesulfonyl chloride. Afterwards, nucleophilic substitution of the sulfonate with NaN3 furnished the Schiff base protected chitosan C6-N3 (BCTS-6-N3). On the other hand, alkynylic β-cyclodextrin (CD-OPg) was obtained by alkynylation of β-cyclodextrin (β-CD). With these two substrates in hand, β-CD was immobilized at the Schiff base protected chitosan 6-OH position via click chemistry between CD-OPg and BCTS-6-N3 to afford BCTS-6-CD, and then chitosan 6-OH immobilized cyclodextrin derivates (CTS-6-CD) was obtained by deprotecting the Schiff base of BCTS-6-CD. The structures of these products were characterized by FTIR, and their crystal properties and thermal stabilities were studied by XRD and TG respectively. By using UV spectroscopy to determine the immobilized amount, we also investigated the effect of the click reaction conditions on the immobilized loading of the synthesized BCTS-6-CD. It was found that the immobilized loading was 197.61 µmol·g−1 in the BCTS-6-CD that was synthesized under the optimum conditions, and it went up to 223.17 µmol·g−1 in CTS-6-CD by deprotecting the Schiff base group.

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Authors and Affiliations

  1. School of Material Science and Engineering, Beijing Institute of Technology, Beijing, 100081, P. R. China

    Yu Chen & Huimin Tan

  2. School of Science, Beijing Institute of Technology, Beijing, 100081, P. R. China

    Yanchun Ye, Ruiru Li & Yanwen Guo

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  1. Yu Chen
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  2. Yanchun Ye
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  3. Ruiru Li
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  4. Yanwen Guo
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  5. Huimin Tan
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Correspondence to Yu Chen.

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Chen, Y., Ye, Y., Li, R. et al. Synthesis of chitosan 6-OH immobilized cyclodextrin derivates via click chemistry. Fibers Polym 14, 1058–1065 (2013). https://doi.org/10.1007/s12221-013-1058-7

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  • DOI: https://doi.org/10.1007/s12221-013-1058-7

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