Abstract
A cellulose paper sheet, chemically modified with azide functions, is described to be a versatile molecular platform for copper-catalyzed 1,3-dipolar cycloaddition with terminal alkynes. This 3-step methodology was carefully optimized at each stage of the process with the support of experimental and physical evidences. Our approach allows the surface coverage of structurally diverse molecular architectures through a covalent grafting with non-hydrolysable chemical linkers. This robust linkage is highlighted with the surface hydrophobization of cellulose paper through the click ligation of cholesterol units as renewable and inexpensive hydrophobic agents. The resulting water-resistant and water-repellent paper-based material shows powerful oleophilicity properties and displays a high contact angle of 139.6°.
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Acknowledgments
We gratefully acknowledge the University of Nantes and the “Centre National de la Recherche Scientifique” (CNRS) for financial support. F.-X. Felpin is a member of the “Institut Universitaire de France” (IUF). M.C. Nongbe thanks the ‘‘Ministère de l’Enseignement Supérieur et de la Recherche Scientifique de Côte d’Ivoire” for a visiting grant in France. We acknowledge Christine Labrugère (PLACAMAT, University of Bordeaux), François-Xavier Lefèvre and Denis Loquet (CEISAM, University of Nantes) for XPS, SEM and elemental analyses, respectively.
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Nongbe, M.C., Bretel, G., Ekou, L. et al. Cellulose paper azide as a molecular platform for versatile click ligations: application to the preparation of hydrophobic paper surface. Cellulose 25, 1395–1411 (2018). https://doi.org/10.1007/s10570-017-1647-5
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DOI: https://doi.org/10.1007/s10570-017-1647-5