Regioselective Protection and Deprotection of Nanocellulose Molecular Design Architecture: Robust Platform for Multifunctional Applications
Autor(a) principal: | |
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Data de Publicação: | 2021 |
Outros Autores: | , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNESP |
Texto Completo: | http://dx.doi.org/10.1021/acs.biomac.1c00909 http://hdl.handle.net/11449/233837 |
Resumo: | 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. |
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Regioselective Protection and Deprotection of Nanocellulose Molecular Design Architecture: Robust Platform for Multifunctional ApplicationsRegioselectively 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.Centre for Biocomposites and Biomaterials Processing John H. Daniels Faculty of Architecture Landscape and Design University of TorontoDepartment of Mechanical and Industrial Engineering University of TorontoDepartment of Mechanical and Aerospace Engineering Carleton UniversityCollege of Agricultural Sciences São Paulo State University (Unesp), BotucatuTOTAL American Services Inc.College of Agricultural Sciences São Paulo State University (Unesp), BotucatuUniversity of TorontoCarleton UniversityUniversidade Estadual Paulista (UNESP)TOTAL American Services Inc.Dias, Otavio Augusto TittonKonar, SamirPakharenko, ViktoriyaGraziano, AntimoLeão, Alcides Lopes [UNESP]Tjong, JimiJaffer, ShaffiqSain, Mohini2022-05-01T11:07:16Z2022-05-01T11:07:16Z2021-01-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://dx.doi.org/10.1021/acs.biomac.1c00909Biomacromolecules.1526-46021525-7797http://hdl.handle.net/11449/23383710.1021/acs.biomac.1c009092-s2.0-85119904242Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengBiomacromoleculesinfo:eu-repo/semantics/openAccess2024-04-30T14:00:18Zoai:repositorio.unesp.br:11449/233837Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T14:18:06.823792Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
Regioselective Protection and Deprotection of Nanocellulose Molecular Design Architecture: Robust Platform for Multifunctional Applications |
title |
Regioselective Protection and Deprotection of Nanocellulose Molecular Design Architecture: Robust Platform for Multifunctional Applications |
spellingShingle |
Regioselective Protection and Deprotection of Nanocellulose Molecular Design Architecture: Robust Platform for Multifunctional Applications Dias, Otavio Augusto Titton |
title_short |
Regioselective Protection and Deprotection of Nanocellulose Molecular Design Architecture: Robust Platform for Multifunctional Applications |
title_full |
Regioselective Protection and Deprotection of Nanocellulose Molecular Design Architecture: Robust Platform for Multifunctional Applications |
title_fullStr |
Regioselective Protection and Deprotection of Nanocellulose Molecular Design Architecture: Robust Platform for Multifunctional Applications |
title_full_unstemmed |
Regioselective Protection and Deprotection of Nanocellulose Molecular Design Architecture: Robust Platform for Multifunctional Applications |
title_sort |
Regioselective Protection and Deprotection of Nanocellulose Molecular Design Architecture: Robust Platform for Multifunctional Applications |
author |
Dias, Otavio Augusto Titton |
author_facet |
Dias, Otavio Augusto Titton Konar, Samir Pakharenko, Viktoriya Graziano, Antimo Leão, Alcides Lopes [UNESP] Tjong, Jimi Jaffer, Shaffiq Sain, Mohini |
author_role |
author |
author2 |
Konar, Samir Pakharenko, Viktoriya Graziano, Antimo Leão, Alcides Lopes [UNESP] Tjong, Jimi Jaffer, Shaffiq Sain, Mohini |
author2_role |
author author author author author author author |
dc.contributor.none.fl_str_mv |
University of Toronto Carleton University Universidade Estadual Paulista (UNESP) TOTAL American Services Inc. |
dc.contributor.author.fl_str_mv |
Dias, Otavio Augusto Titton Konar, Samir Pakharenko, Viktoriya Graziano, Antimo Leão, Alcides Lopes [UNESP] Tjong, Jimi Jaffer, Shaffiq Sain, Mohini |
description |
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. |
publishDate |
2021 |
dc.date.none.fl_str_mv |
2021-01-01 2022-05-01T11:07:16Z 2022-05-01T11:07:16Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://dx.doi.org/10.1021/acs.biomac.1c00909 Biomacromolecules. 1526-4602 1525-7797 http://hdl.handle.net/11449/233837 10.1021/acs.biomac.1c00909 2-s2.0-85119904242 |
url |
http://dx.doi.org/10.1021/acs.biomac.1c00909 http://hdl.handle.net/11449/233837 |
identifier_str_mv |
Biomacromolecules. 1526-4602 1525-7797 10.1021/acs.biomac.1c00909 2-s2.0-85119904242 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Biomacromolecules |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.source.none.fl_str_mv |
Scopus reponame:Repositório Institucional da UNESP instname:Universidade Estadual Paulista (UNESP) instacron:UNESP |
instname_str |
Universidade Estadual Paulista (UNESP) |
instacron_str |
UNESP |
institution |
UNESP |
reponame_str |
Repositório Institucional da UNESP |
collection |
Repositório Institucional da UNESP |
repository.name.fl_str_mv |
Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP) |
repository.mail.fl_str_mv |
|
_version_ |
1808128343035346944 |