Canale-Salazar, I, Lizardi-Mendoza, J, López-Franco, Y et al. (4 more authors) (2020) Synthesis of regioselective chitosan copolymers with β-cyclodextrin and poly(N-isopropyl acrylamide). Journal of Polymer Research, 27 (5). 112. ISSN 1022-9760
Abstract
This work aimed to design a synthetic route under mild conditions allowing the main chitosan chain to be grafted with β-cyclodextrin (β-CD) and poly(N-isopropyl acrylamide) (PNIPAm), at C2 and C6 positions, respectively. For this reason, the regioselectivity of proposed reactions is an important factor to be considered. β-CD is an oligosaccharide with a cyclic structure capable of forming inclusion complexes with hydrophobic molecules. Grafting β-CD onto the chitosan backbone by reductive N-alkylation at C2 position was carried out. With this purpose, the previous preparation of β-CD monoaldehyde was required. PNIPAm is a thermosensitive polymer with a transition temperature near 33 °C. To regioselectively anchor poly(N-isopropyl acrylamide) chains onto chitosan at C6 position, it was required to attach at the C6 position of chitosan an alkyl group for the subsequent grafting of PNIPAm-N3 by means of copper-catalyzed azide-alkyne cycloaddition click reaction. To guarantee the regioselectivity of the functionalization of chitosan with a C6 terminal alkyne, its oxyalkylation with glycidyl propargyl ether in a solvent composed of LiOH/KOH/urea was used. The structure of all derivatives was confirmed by FT-IR and 1H-NMR spectroscopy.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © The Polymer Society, Taipei 2020. This is an author produced version of a rapid communication published in Journal of Polymer Research. Uploaded in accordance with the publisher's self-archiving policy. |
Keywords: | Chitosan copolymer; β-cyclodextrin; Poly(N-isopropyl acrylamide); Click chemistry; Regioselectivity |
Dates: |
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Institution: | The University of Leeds |
Academic Units: | The University of Leeds > Faculty of Environment (Leeds) > School of Food Science and Nutrition (Leeds) > FSN Chemistry and Biochemistry (Leeds) |
Depositing User: | Symplectic Publications |
Date Deposited: | 05 Nov 2021 09:31 |
Last Modified: | 25 Jun 2023 22:48 |
Status: | Published |
Publisher: | Springer |
Identification Number: | 10.1007/s10965-020-02076-7 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:179788 |