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Regioselective Protection and Deprotection of Nanocellulose Molecular Design Architecture: Robust Platform for Multifunctional Applications
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    Regioselective Protection and Deprotection of Nanocellulose Molecular Design Architecture: Robust Platform for Multifunctional Applications
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    • Otavio Augusto Titton Dias*
      Otavio Augusto Titton Dias
      Centre for Biocomposites and Biomaterials Processing, John H. Daniels Faculty of Architecture, Landscape, and Design, University of Toronto, Toronto, Ontario M5S 3B3, Canada
      *Email: [email protected]
    • Samir Konar
      Samir Konar
      Centre for Biocomposites and Biomaterials Processing, John H. Daniels Faculty of Architecture, Landscape, and Design, University of Toronto, Toronto, Ontario M5S 3B3, Canada
      Department of Mechanical and Industrial Engineering, University of Toronto, Toronto, Ontario M5S3G8, Canada
      More by Samir Konar
    • Viktoriya Pakharenko
      Viktoriya Pakharenko
      Centre for Biocomposites and Biomaterials Processing, John H. Daniels Faculty of Architecture, Landscape, and Design, University of Toronto, Toronto, Ontario M5S 3B3, Canada
    • Antimo Graziano
      Antimo Graziano
      Department of Mechanical and Aerospace Engineering, Carleton University, Ottawa, Ontario K1S 5B6, Canada
    • Alcides Lopes Leão
      Alcides Lopes Leão
      College of Agricultural Sciences, São Paulo State University (Unesp), Botucatu, São Paulo 18610307, Brazil
    • Jimi Tjong
      Jimi Tjong
      Department of Mechanical and Industrial Engineering, University of Toronto, Toronto, Ontario M5S3G8, Canada
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    • Shaffiq Jaffer
      Shaffiq Jaffer
      TOTAL American Services Inc., Hopkinton, Massachusetts 01748, United States
    • Mohini Sain
      Mohini Sain
      Centre for Biocomposites and Biomaterials Processing, John H. Daniels Faculty of Architecture, Landscape, and Design, University of Toronto, Toronto, Ontario M5S 3B3, Canada
      Department of Mechanical and Industrial Engineering, University of Toronto, Toronto, Ontario M5S3G8, Canada
      More by Mohini Sain
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    Biomacromolecules

    Cite this: Biomacromolecules 2021, 22, 12, 4980–4987
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    https://doi.org/10.1021/acs.biomac.1c00909
    Published November 18, 2021
    Copyright © 2021 American Chemical Society

    Abstract

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    Regioselectively substituted nanocellulose was synthesized by protecting the primary hydroxyl group. Herein, we took advantage of the different reactivities of primary and secondary hydroxyl groups to graft large capping structures. This study mainly focuses on regioselective installation of trityl protecting groups on nanocellulose chains. The elemental analysis and nuclear magnetic resonance spectroscopy of regioselectively substituted nanofibrillated cellulose (NFC) suggested that the trityl group was successfully grafted in the primary hydroxyl group with a degree of substitution of nearly 1. Hansen solubility parameters were employed, and the binary system composed of an ionic liquid and pyridine as a base was revealed to be the optimum condition for regioselective functionalization of nanocellulose. Interestingly, the dissolution of NFC in the ionic liquid and the subsequent deprotection process of NFC substrates hardly affected the crystalline structure of NFC (3.6% decrease in crystallinity). This method may provide endless possibilities for the design of advanced engineered nanomaterials with multiple functionalities. We envisage that this protection/deprotection approach may lead to a bright future for the fabrication of multifunctional devices based on nanocellulose.

    Copyright © 2021 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.biomac.1c00909.

    • Abbreviations; scheme displaying the fabrication of NFC using an ultrafine friction grinder supermasscolloider; images of NFC slurry and reaction mixture; calculation of the degree of substitution of tritylated NFC; calculation of Cr and crystallite size of the samples; TEM images of NFC and tritylated NFC; and visual appearance of the casted films (PDF)

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    Cited By

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    This article is cited by 3 publications.

    1. Qianqian Wang, Lin Zhong, Yang Zhou, Shixuan Feng, Jun Liu, Huan Liu, Qianqian Zhu. Regioselective functionalization of cellulose nanomaterial for advanced application. Carbohydrate Polymers 2025, 348 , 122889. https://doi.org/10.1016/j.carbpol.2024.122889
    2. Otavio Augusto Titton Dias, Samir Konar, Viktoriya Pakharenko, Antimo Graziano, Alcides Lopes Leão, Jimi Tjong, Shaffiq Jaffer, Teng Cui, Tobin Filleter, Mohini Sain. Molecular design and structural optimization of nanocellulose-based films fabricated via regioselective functionalization for flexible electronics. Chemical Engineering Journal 2022, 440 , 135950. https://doi.org/10.1016/j.cej.2022.135950
    3. Xudong GAO, Yanan JIA, Zhongqin CHEN, Ramesh Kumar SANTHANAM, Min ZHANG, Chengwei HE, Haixia CHEN. Synthesis of hydrogels based on nanocellulose from garlic straw and regulating the release of allicin and its cytotoxicity. Food Science and Technology 2022, 42 https://doi.org/10.1590/fst.43422

    Biomacromolecules

    Cite this: Biomacromolecules 2021, 22, 12, 4980–4987
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.biomac.1c00909
    Published November 18, 2021
    Copyright © 2021 American Chemical Society

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