Abstract
This paper presents an environmentally friendly strategy to obtain alkynylated cellulose fibers (ACFs), a versatile platform for tailoring cellulose by robust click reaction. This strategy is based on the integration of two efficient reactions: selective oxidation of cellulose fibers by sodium periodate (NaIO4) generating dialdehyde cellulose fibers and subsequent Schiff base reaction with 3-ethynylaniline yielding alkynylated cellulose fibers (ACFs). The alkynyl moieties introduced into ACFs were simply transferred with azido compounds under Cu(I) catalysis and mild conditions. The content of alkynyl groups of ACFs was found to be as high as 3.0 mmol/g. Fourier transform infrared spectroscopy (FTIR) showed that the selective oxidation of cellulose fibers generated aldehyde groups and the Schiff base reaction resulted in the incorporation of ethynyl groups and benzene rings into cellulose fibers. FTIR and X-ray photoelectron spectroscopy results confirmed the successful click reaction between ACFs and 4-azidobenzoic acid. This clickable platform would serve as a versatile starting precursor for finely tuning cellulose fibers for advanced applications.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Abd Rahman NS, Ahmad NA, Yhaya MF, Azahari B, Ismail WR (2016) Crosslinking of fibers via azide–alkyne click chemistry: synthesis and characterization. J Appl Polym Sci 133:43576. doi:10.1002/app.43576
Anastas P, Eghbali N (2010) Green chemistry: principles and practice. Chem Soc Rev 39:301–312. doi:10.1039/b918763b
Anseth KS, Klok HA (2016) Click chemistry in biomaterials, nanomedicine, and drug delivery. Biomacromol 17:1–3. doi:10.1021/acs.biomac.5b01660
Dash R, Elder T, Ragauskas A (2012) Grafting of model primary amine compounds to cellulose nanowhiskers through periodate oxidation. Cellulose 19:2069–2079. doi:10.1007/s10570-012-9769-2
Elchinger PH, Faugeras PA, Boëns B, Brouillette F, Montplaisir D, Zerrouki R, Lucas R (2011) Polysaccharides: the “click” chemistry impact. Polymers 3:1607–1651. doi:10.3390/polym3041607
Elchinger PH, Awada H, Zerrouki C, Montplaisir D, Zerrouki R (2014) Kraft pulp-starch covalent linking: a promising route to a new material. Ind Eng Chem Res 53:7604–7610. doi:10.1021/ie500555g
Feese E, Sadeghifar H, Gracz HS, Argyropoulos DS, Ghiladi RA (2011) Photobactericidal porphyrin-cellulose nanocrystals: synthesis, characterization, and antimicrobial properties. Biomacromol 12:3528–3539. doi:10.1021/bm200718s
Filpponen I, Argyropoulos DS (2010) Regular linking of cellulose nocrystals via click chemistry synthesis and formation cellulose nanoplatelet gels. Biomacromol 11:1060–1066. doi:10.1021/bm1000247
Filpponen I, Sadeghifar H, Argyropoulos DS (2011) Photoresponsive cellulose nanocrystals. Nanomater Nanotechnol 1:34–43
Hafren J, Zou W, Cordova A (2006) Heterogeneous ‘organoclick’ derivatization of polysaccharides. Macromol Rapid Commun 27:1362–1366. doi:10.1002/marc.200600328
Hou QX, Liu W, Liu ZH, Bai LL (2007) Characteristics of wood cellulose fibers treated with periodate and bisulfite. Ind Eng Chem Res 46:7830–7837. doi:10.1021/ie0704750
Karaaslan MA, Gao G, Kadla JF (2013) Nanocrystalline cellulose/β-casein conjugated nanoparticles prepared by click chemistry. Cellulose 20:2655–2665. doi:10.1007/s10570-013-0065-6
Kolb HC, Finn MG, Sharpless KB (2001) Click chemistry diverse chemical function from a few good reactions. Angew Chem Int Ed 40:2004–2021
Liebert T, Hänsch C, Heinze T (2006) Click chemistry with polysaccharides. Macromol Rapid Commun 27:208–213. doi:10.1002/marc.200500686
Mangiante G, Alcouffe P, Burdin B, Gaborieau M, Zeno E, Petit-Conil M, Bernard J, Charlot A, Fleury E (2013) Green nondegrading approach to alkyne-functionalized cellulose fibers and biohybrids thereof: synthesis and mapping of the derivatization. Biomacromol 14:254–263. doi:10.1021/bm3016829
Meng X, Edgar KJ (2016) “Click” reactions in polysaccharide modification. Prog Polym Sci 53:52–85. doi:10.1016/j.progpolymsci.2015.07.006
Pahimanolis N, Hippi U, Johansson LS, Saarinen T, Houbenov N, Ruokolainen J, Seppälä J (2011) Surface functionalization of nanofibrillated cellulose using click-chemistry approach in aqueous media. Cellulose 18:1201–1212. doi:10.1007/s10570-011-9573-4
Pohl M, Schaller J, Meister F, Heinze T (2008) Selectively dendronized cellulose: synthesis and characterization. Macromol Rapid Commun 29:142–148. doi:10.1002/marc.200700628
Qi HS, Yang QL, Zhang LN, Liebert T, Heinze T (2011) The dissolution of cellulose in NaOH-based aqueous system by two-step process. Cellulose 18:237–245. doi:10.1007/s10570-010-9477-8
Ringot C, Sol V, Granet R, Krausz P (2009) Porphyrin-grafted cellulose fabric: new photobactericidal material obtained by “Click-chemistry” reaction. Mater Lett 63:1889–1891. doi:10.1016/j.matlet.2009.06.009
Schmidt S, Liebert T, Heinze T (2014) Synthesis of soluble cellulose tosylates in an eco-friendly medium. Green Chem 16:1941. doi:10.1039/c3gc41994k
Shi S, He F (2003) Pulping and papermaking analysis and testing. China Light Industry Press, Beijing (in Chinese)
Sirvio J, Hyvakko U, Liimatainen H, Niinimaki J, Hormi O (2011) Periodate oxidation of cellulose at elevated temperatures using metal salts as cellulose activators. Carbohydr Polym 83:1293–1297. doi:10.1016/j.carbpol.2010.09.036
Swatloski RP, Spear SK, Holbrey JD, Rogers RD (2002) Dissolution of cellulose with ionic liquids. J Am Chem Soc 124:4974–4975. doi:10.1021/ja025790m
Syverud K, Pettersen SR, Draget K, Chinga-Carrasco G (2015) Controlling the elastic modulus of cellulose nanofibril hydrogels—scaffolds with potential in tissue engineering. Cellulose 22:473–481. doi:10.1007/s10570-014-0470-5
Wang H, Gurau G, Rogers RD (2012) Ionic liquid processing of cellulose. Chem Soc Rev 41:1519–1537. doi:10.1039/c2cs15311d
Xu W, Gao G, Kadla J (2013) Synthesis of antibacterial cellulose materials using a “clickable” quaternary ammonium compound. Cellulose 20:1187–1191. doi:10.1007/s10570-013-9914-6
Yadav P, Chacko S, Kumar G, Ramapanicker R, Verma V (2015) Click chemistry route to covalently link cellulose and clay. Cellulose 22:1615–1624. doi:10.1007/s10570-015-0594-2
Yang H, van de Ven TGM (2016) A bottom-up route to a chemically end-to-end assembly of nanocellulose fibers. Biomacromol 17:2240–2247. doi:10.1021/acs.biomac.6b00480
Acknowledgments
The authors would like to acknowledge the financial support of the National Natural Science Foundation of China (31370579).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Ding, C., Sun, L., Xiao, G. et al. Green and combinational method towards clickable alkynylated cellulose fibers (ACFs). Cellulose 24, 3219–3229 (2017). https://doi.org/10.1007/s10570-017-1363-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10570-017-1363-1