ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Figure 1Loading Img
RETURN TO ISSUEPREVResearch ArticleNEXT

Lignin-Inspired Surface Modification of Nanocellulose by Enzyme-Catalyzed Radical Coupling of Coniferyl Alcohol in Pickering Emulsion

Cite this: ACS Sustainable Chem. Eng. 2020, 8, 2, 1185–1194
Publication Date (Web):December 16, 2019
https://doi.org/10.1021/acssuschemeng.9b06291
Copyright © 2019 American Chemical Society

    Article Views

    1874

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options
    Supporting Info (1)»

    Abstract

    Abstract Image

    A biomimetic approach to the surface modification of nanocellulose is proposed. This strategy was inspired by plant cell wall lignification, in which lignin, a hydrophobic biopolymer, tightly assembles cellulose microfibrils and matrix polysaccharides to confer the cell walls with essential mechanical properties. Enzymatic dehydrogenative polymerization of coniferyl alcohol in a nanocellulose-stabilized oil-in-water Pickering emulsion system efficiently yielded hydrophobic dehydrogenative polymers (DHPs) on hydrophilic nanocellulose without any phase separation. The DHPs were formed at the oil–water interface, where nanocellulose acted as a solid surfactant, covering the surface of the emulsion particles. DHP-integrated nanocellulose was casted to form thin films, with water contact angles on the as-prepared films increased by DHP incorporation, demonstrating the successful modulation of hydrophilicity of nanocellulose. In-depth structural analysis of DHPs by heteronuclear single quantum coherence (HSQC) NMR demonstrated that β-5 linkages were markedly increased compared with β-O-4 and β–β linkages in DHPs prepared using the nanocellulose-assisted Pickering emulsion system, while DHPs prepared using conventional nonemulsion polymerization systems were barely influenced by the presence of nanocellulose. These results suggested that nanocellulose acted as an efficient scaffold for monolignol radical coupling at the interface of the oil-in-water Pickering emulsion system, which provides new insight into the surface modification of nanocellulose in a biomimetic fashion.

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Supporting Information

    ARTICLE SECTIONS
    Jump To

    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acssuschemeng.9b06291.

    • Microscopic images of Pickering emulsion, chemical structures of dyes, photographs of DHP–nanocellulose samples in Wiesner staining test, fluorescence, and TEM images of samples, photographs of reaction media and water droplets on DHP–nanocellulose films, polarized optical microscopy images of the films, NMR spectra of samples, GPC profiles of samples, and molecular weight data of samples (PDF)

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 17 publications.

    1. Mariam Sohail, Tahira Pirzada, Richard Guenther, Eduardo Barbieri, Tim Sit, Stefano Menegatti, Nathan Crook, Charles H. Opperman, Saad A. Khan. Cellulose Acetate-Stabilized Pickering Emulsions: Preparation, Rheology, and Incorporation of Agricultural Active Ingredients. ACS Sustainable Chemistry & Engineering 2023, 11 (42) , 15178-15191. https://doi.org/10.1021/acssuschemeng.3c02428
    2. Hanaé Dupont, Valentin Maingret, Véronique Schmitt, Valérie Héroguez. New Insights into the Formulation and Polymerization of Pickering Emulsions Stabilized by Natural Organic Particles. Macromolecules 2021, 54 (11) , 4945-4970. https://doi.org/10.1021/acs.macromol.1c00225
    3. Yuna Tanaka, Qi Li, Mayumi Hatakeyama, Takuya Kitaoka. Synthesis and structural design of microspheres comprising cellulose nanofibers and artificial lignin polymer by enzyme-mediated Pickering emulsion templating. RSC Sustainability 2024, 2 (5) , 1580-1589. https://doi.org/10.1039/D4SU00067F
    4. Danial Khorsandi, Serena Jenson, Atefeh Zarepour, Arezoo Khosravi, Navid Rabiee, Siavash Iravani, Ali Zarrabi. Catalytic and biomedical applications of nanocelluloses: A review of recent developments. International Journal of Biological Macromolecules 2024, 18 , 131829. https://doi.org/10.1016/j.ijbiomac.2024.131829
    5. Peipei Liu, Chunling Zheng, Zhong Yao, Fang Zhang. A Biomimetic Lignocellulose Aerogel-Based Membrane for Efficient Phenol Extraction from Water. Gels 2024, 10 (1) , 59. https://doi.org/10.3390/gels10010059
    6. Fang Zhang, Yuxin Sun, Xinye Qian, Xiaoyan Tan, Peipei Liu, Zhong Yao, Chunling Zheng, Yonghong Hu. Stable and easily detachable cellulose-based membrane system inspired by water hyacinth for efficient heavy metals removal from water. Cellulose 2023, 30 (18) , 11619-11632. https://doi.org/10.1007/s10570-023-05579-w
    7. Chuye Ji, Yixiang Wang. Nanocellulose-stabilized Pickering emulsions: Fabrication, stabilization, and food applications. Advances in Colloid and Interface Science 2023, 318 , 102970. https://doi.org/10.1016/j.cis.2023.102970
    8. Feng Tang, Young Gyu Jeong. Interface‐engineered polypropylene/cellulose nanofibril composites with enhanced thermal stability, mechanical modulus, and impact strength. Polymer Composites 2023, 44 (1) , 190-201. https://doi.org/10.1002/pc.27038
    9. Sunil K. Sharma, Priyanka R. Sharma, Likun Wang, Micheal Pagel, William Borges, Ken I. Johnson, Aniket Raut, Kevin Gu, Chulsung Bae, Miriam Rafailovich, Benjamin S. Hsiao. Nitro-oxidized carboxylated cellulose nanofiber based nanopapers and their PEM fuel cell performance. Sustainable Energy & Fuels 2022, 6 (15) , 3669-3680. https://doi.org/10.1039/D2SE00442A
    10. Qi Li, Mayumi Hatakeyama, Takuya Kitaoka. Bioadaptive Porous 3D Scaffolds Comprising Cellulose and Chitosan Nanofibers Constructed by Pickering Emulsion Templating. Advanced Functional Materials 2022, 32 (22) https://doi.org/10.1002/adfm.202200249
    11. R.A. Ilyas, S.M. Sapuan, M.S. Ibrahim, M.H. Wondi, M.N.F. Norrrahim, M.M. Harussani, H.A. Aisyah, M.A. Jenol, Z. Nahrul Hayawin, M.S.N. Atikah, R. Ibrahim, S.O.A. SaifulAzry, C.S. Hassan, N.I.N. Haris. Introduction to oil palm biomass. 2022, 3-38. https://doi.org/10.1016/B978-0-12-823852-3.00015-5
    12. Kevin De France, Zhihui Zeng, Tingting Wu, Gustav Nyström. Functional Materials from Nanocellulose: Utilizing Structure–Property Relationships in Bottom‐Up Fabrication. Advanced Materials 2021, 33 (28) https://doi.org/10.1002/adma.202000657
    13. Ning Sun, Qiuhong Li, Zhaoyu Zhang, Shujin Ge, Xiujie Chang, Mingchi Yu, Aixiang Li, Yanfei Ma. Construction, modulation and transition of light responsive oil-in-water novel emulsions stabilized by similarly charged nanoparticles and dye molecules. Colloids and Surfaces A: Physicochemical and Engineering Aspects 2021, 619 , 126494. https://doi.org/10.1016/j.colsurfa.2021.126494
    14. E. Gerbin, G.N. Rivière, L. Foulon, Y.M. Frapart, B. Cottyn, M. Pernes, C. Marcuello, B. Godon, A. Gainvors-Claisse, D. Crônier, A. Majira, M. Österberg, B. Kurek, S. Baumberger, V. Aguié-Béghin. Tuning the functional properties of lignocellulosic films by controlling the molecular and supramolecular structure of lignin. International Journal of Biological Macromolecules 2021, 181 , 136-149. https://doi.org/10.1016/j.ijbiomac.2021.03.081
    15. Fuqiang Chang, Carolien M. Vis, Wirawan Ciptonugroho, Pieter C. A. Bruijnincx. Recent developments in catalysis with Pickering Emulsions. Green Chemistry 2021, 23 (7) , 2575-2594. https://doi.org/10.1039/D0GC03604H
    16. Naoya Fukuda, Mayumi Hatakeyama, Takuya Kitaoka. Enzymatic Preparation and Characterization of Spherical Microparticles Composed of Artificial Lignin and TEMPO-Oxidized Cellulose Nanofiber. Nanomaterials 2021, 11 (4) , 917. https://doi.org/10.3390/nano11040917
    17. Fatima A. Hussein, Safanah S. Jaafar, Wafaa M. Salih. Synthesis and characterization of CNC-cefexime nanohybrid as a potential antibacterial agent. Materials Today: Proceedings 2021, 45 , 5564-5568. https://doi.org/10.1016/j.matpr.2021.02.308

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect