Abstract
Hydroxyethyl cellulose (HEC) is considered one of the most important hydro-soluble cellulose derivatives, thanks to its biocompatibility and biodegradability profile. In this work, a facile synthesis methodology was developed to graft ionic liquids onto the HEC ester. Firstly, a low Tg (glass transition temperature) glassy brominated hydrophobic ester based on HEC was prepared. By regioselective nucleophilic substitution of bromine with imidazole and pyridine derivatives, HEC-ILs (ionic liquids) with a high degree of substitution were elaborated in a second step. The synthesized HEC-ILs were characterized by nuclear magnetic resonance (1H, 13C NMR), elemental analysis (CHNO), Fourier transform infrared spectroscopy-Attenuated total reflection (FTIR-ATR), X-ray diffraction, thermogravimetric analysis, differential scanning calorimetry and scanning electron microscopy. Zeta potential was used to verify the presence of permanent positive charge. Contact angle measurements were exploited to follow the reorganization of the surface of HEC-ILs in contact with water. A theoretical study was carried out to investigate the intra- and intermolecular interactions of polymer chains. The prepared cationic HEC derivatives have attractive properties such as their amphiphilic and glassy character, solubility in water, and a permanent positive charge. Such properties open a wide range of applications in the field of drug delivery and the complexation of anionic molecules.
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Acknowledgments
A special thanks to the reviewers for their remarks, pieces advice and comments on the manuscript. The authors would like to thank the head of the department of chemistry Prof. Abdelmonaem TALHAOUI for making the analytical platform open for the researchers to do all the necessary analyses. We would like also to thank Mr. ACHALHI Achraf for his writing assistance, language editing, and proofreading.
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This research was partially supported and funded by Mohamed Ist University projects PARA I&II, CNRST and Etelä-Karjala Säästöpankki Foundation, Finland.
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NA: experimental part, investigation, writing, validation. YEO: characterization part, investigation, validation. REY: investigation, validation. ML: theoretical study, writing. SEB: supervision, formal analysis, correction. KL: Formal analysis, data curation, validation. AEI: supervision, formal analysis, writing-review and editing.
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Achalhi, N., El Ouardi, Y., El Yousfi, R. et al. An efficient pathway to the elaboration of glassy amphiphilic ester based hydroxyethyl cellulose and ionic liquids. Cellulose 30, 1483–1502 (2023). https://doi.org/10.1007/s10570-022-04988-7
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DOI: https://doi.org/10.1007/s10570-022-04988-7