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Regioselective and water-assisted surface esterification of never-dried cellulose: nanofibers with adjustable surface energy

A new regioselective route is introduced for surface modification of biological colloids in the presence of water. Taking the case of cellulose nanofibers (CNFs), we demonstrate a site-specific (93% selective) reaction between the primary surface hydroxyl groups (C6-OH) of cellulose and acyl imidazo...

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Autores principales: Beaumont, Marco, Otoni, Caio G., Mattos, Bruno D., Koso, Tetyana V., Abidnejad, Roozbeh, Zhao, Bin, Kondor, Anett, King, Alistair W. T., Rojas, Orlando J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8452180/
https://www.ncbi.nlm.nih.gov/pubmed/34671224
http://dx.doi.org/10.1039/d1gc02292j
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author Beaumont, Marco
Otoni, Caio G.
Mattos, Bruno D.
Koso, Tetyana V.
Abidnejad, Roozbeh
Zhao, Bin
Kondor, Anett
King, Alistair W. T.
Rojas, Orlando J.
author_facet Beaumont, Marco
Otoni, Caio G.
Mattos, Bruno D.
Koso, Tetyana V.
Abidnejad, Roozbeh
Zhao, Bin
Kondor, Anett
King, Alistair W. T.
Rojas, Orlando J.
author_sort Beaumont, Marco
collection PubMed
description A new regioselective route is introduced for surface modification of biological colloids in the presence of water. Taking the case of cellulose nanofibers (CNFs), we demonstrate a site-specific (93% selective) reaction between the primary surface hydroxyl groups (C6-OH) of cellulose and acyl imidazoles. CNFs bearing C6-acetyl and C6-isobutyryl groups, with a degree of substitution of up to 1 mmol g(−1) are obtained upon surface esterification, affording CNFs of adjustable surface energy. The morphological and structural features of the nanofibers remain largely unaffected, but the regioselective surface reactions enable tailoring of their interfacial interactions, as demonstrated in oil/water Pickering emulsions. Our method precludes the need for drying or exchange with organic solvents for surface esterification, otherwise needed in the synthesis of esterified colloids and polysaccharides. Moreover, the method is well suited for application at high-solid content, opening the possibility for implementation in reactive extrusion and compounding. The proposed acylation is introduced as a sustainable approach that benefits from the presence of water and affords a high chemical substitution selectivity.
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spelling pubmed-84521802021-10-18 Regioselective and water-assisted surface esterification of never-dried cellulose: nanofibers with adjustable surface energy Beaumont, Marco Otoni, Caio G. Mattos, Bruno D. Koso, Tetyana V. Abidnejad, Roozbeh Zhao, Bin Kondor, Anett King, Alistair W. T. Rojas, Orlando J. Green Chem Chemistry A new regioselective route is introduced for surface modification of biological colloids in the presence of water. Taking the case of cellulose nanofibers (CNFs), we demonstrate a site-specific (93% selective) reaction between the primary surface hydroxyl groups (C6-OH) of cellulose and acyl imidazoles. CNFs bearing C6-acetyl and C6-isobutyryl groups, with a degree of substitution of up to 1 mmol g(−1) are obtained upon surface esterification, affording CNFs of adjustable surface energy. The morphological and structural features of the nanofibers remain largely unaffected, but the regioselective surface reactions enable tailoring of their interfacial interactions, as demonstrated in oil/water Pickering emulsions. Our method precludes the need for drying or exchange with organic solvents for surface esterification, otherwise needed in the synthesis of esterified colloids and polysaccharides. Moreover, the method is well suited for application at high-solid content, opening the possibility for implementation in reactive extrusion and compounding. The proposed acylation is introduced as a sustainable approach that benefits from the presence of water and affords a high chemical substitution selectivity. The Royal Society of Chemistry 2021-08-02 /pmc/articles/PMC8452180/ /pubmed/34671224 http://dx.doi.org/10.1039/d1gc02292j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Beaumont, Marco
Otoni, Caio G.
Mattos, Bruno D.
Koso, Tetyana V.
Abidnejad, Roozbeh
Zhao, Bin
Kondor, Anett
King, Alistair W. T.
Rojas, Orlando J.
Regioselective and water-assisted surface esterification of never-dried cellulose: nanofibers with adjustable surface energy
title Regioselective and water-assisted surface esterification of never-dried cellulose: nanofibers with adjustable surface energy
title_full Regioselective and water-assisted surface esterification of never-dried cellulose: nanofibers with adjustable surface energy
title_fullStr Regioselective and water-assisted surface esterification of never-dried cellulose: nanofibers with adjustable surface energy
title_full_unstemmed Regioselective and water-assisted surface esterification of never-dried cellulose: nanofibers with adjustable surface energy
title_short Regioselective and water-assisted surface esterification of never-dried cellulose: nanofibers with adjustable surface energy
title_sort regioselective and water-assisted surface esterification of never-dried cellulose: nanofibers with adjustable surface energy
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8452180/
https://www.ncbi.nlm.nih.gov/pubmed/34671224
http://dx.doi.org/10.1039/d1gc02292j
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