Cellulose Functionalization Using N-Heterocyclic-Based Leaving Group Chemistry

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Journal Title
Journal ISSN
Volume Title
A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä
Date
2024-01
Major/Subject
Mcode
Degree programme
Language
en
Pages
25
Series
Polymers, Volume 16, issue 1
Abstract
There has been continuous interest in developing novel activators that facilitate the functionalization of cellulosic materials. In this paper, we developed a strategy in which trisubstituted triazinium salts act as cellulose preactivators. As leaving groups, these triazinium salts utilize N-heterocycles (pyridine, imidazole, and nicotinic acid). Initially, we optimized the synthetic route for developing these novel cellulose preactivators (triazinium salts), whose structures were confirmed using NMR spectroscopy. The surface zeta potential of cellulose changed from a negative value to a positive one after preactivation due to the cationic nature of these preactivators. To enhance the scope of the study, we functionalized the cellulose-preactivated materials with a series of amine- or hydroxy-containing aliphatic and aromatic hydrocarbons, nucleophilic amino acids (cysteine), colorants (2-aminoanthraquinone and 2-amino-3-methyl-anthraquinone), and biopolymer (zein protein). The treated samples were analyzed using FTIR, time-gated Raman spectroscopy, and reflection spectroscopy, and the success of the functionalization process was validated. To widen the scope of such chemistries, we synthesized four reactive agents containing N-heterocyclic-based leaving groups (pyridine and nicotinic acid) and successfully functionalized cellulose with them in one step. The proposed single- and two-step functionalization approaches will provide opportunities for chemically linking various chemical compounds to cellulose for different applications.
Description
Funding Information: The authors would like to thank FinnCERES, the flagship program of Academy of Finland. Publisher Copyright: © 2024 by the authors.
Keywords
activators, cellulose chemistry, cellulose functionalization, coloration, leaving group chemistry, surface modification
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Citation
Negi, A & Tehrani-Bagha, A R 2024, ' Cellulose Functionalization Using N-Heterocyclic-Based Leaving Group Chemistry ', Polymers, vol. 16, no. 1, 149 . https://doi.org/10.3390/polym16010149