Regioselective Protection and Deprotection of Nanocellulose Molecular Design Architecture: Robust Platform for Multifunctional Applications
- Otavio Augusto Titton Dias*
- Samir KonarSamir KonarCentre for Biocomposites and Biomaterials Processing, John H. Daniels Faculty of Architecture, Landscape, and Design, University of Toronto, Toronto, Ontario M5S 3B3, CanadaDepartment of Mechanical and Industrial Engineering, University of Toronto, Toronto, Ontario M5S3G8, CanadaMore by Samir Konar
- Viktoriya Pakharenko
- Antimo GrazianoAntimo GrazianoDepartment of Mechanical and Aerospace Engineering, Carleton University, Ottawa, Ontario K1S 5B6, CanadaMore by Antimo Graziano
- Alcides Lopes LeãoAlcides Lopes LeãoCollege of Agricultural Sciences, São Paulo State University (Unesp), Botucatu, São Paulo 18610307, BrazilMore by Alcides Lopes Leão
- Jimi Tjong
- Shaffiq Jaffer
- , and
- Mohini SainMohini SainCentre for Biocomposites and Biomaterials Processing, John H. Daniels Faculty of Architecture, Landscape, and Design, University of Toronto, Toronto, Ontario M5S 3B3, CanadaDepartment of Mechanical and Industrial Engineering, University of Toronto, Toronto, Ontario M5S3G8, CanadaMore by Mohini Sain
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.
This article is cited by 2 publications.
- 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
- 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