Top

Cellulose

Published in:

10-12-2016 | Original Paper

Facile strategy for preparation of alkyne-functionalized cellulose fibers with click reactivity

Authors: Guifa Xiao, Chunyue Ding, Feiyu Song, Xueren Qian, Xianhui An

Published in: Cellulose | Issue 2/2017

Activate our intelligent search to find suitable subject content or patents.

search-config

AI-assisted search

Off

Abstract

A facile strategy for preparation of alkyne-functionalized cellulose fibers with click reactivity is reported herein. Poly(3-ethynylaniline) [poly(3-EA)] with pendant alkynyl groups was obtained by chemical oxidation polymerization of 3-ethynylaniline with ammonium persulfate in low-concentration hydrochloric acid solution at ice-bath temperature and used to generate alkyne-functionalized cellulose fibers in situ from pulp fibres. Successful preparation of alkyne-functionalized cellulose fibers was confirmed by attenuated total reflectance Fourier-transform infrared spectroscopy, X-ray photoelectron spectroscopy, and scanning electron microscopy. The effects of process variables on poly(3-EA) deposition and fiber loss were investigated, and suitable preparation conditions identified. Deposition of poly(3-EA) did not change the crystallinity or hydrophilicity of the cellulose fibers. Poly(3-EA) and alkyne-functionalized cellulose fibers reacted with azides by Cu(I)-catalyzed alkyne–azide 1,3-dipolar cycloaddition. Thus, this in situ chemical polymerization technology provides a new platform for click functionalization of cellulose fibers. Applications of cellulose fibers produced in this way are limited to those without demanding requirements in terms of product strength or color.

previous article Cellulose dissolution: insights on the contributions of solvent-induced decrystallization and chain disentanglement

next article Synthesis and characterization of alkyl cellulose ω-carboxyesters for amorphous solid dispersion

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

inform now

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

inform now

Agag T, Vietmeier K, Chernykh A, Ishida H (2012) Side-chain type benzoxazine-functional cellulose via click chemistry. J Appl Polym Sci 125:1346–1351CrossRef

Agard NJ, Prescher JA, Bertozzi CR (2004) A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems. J Am Chem Soc 126:15046–15047CrossRef

Alila S, Ferraria AM, do Rego AMB, Boufi S (2009) Controlled surface modification of cellulose fibers by amino derivatives using N,N′-carbonyldiimidazole as activator. Carbohydr Polym 77:553–562CrossRef

Belgacem MN, Gandini A (eds) (2008) Surface modification of cellulose fibres. In: Monomers, polymers and composites from renewable resources. Elsevier, Amsterdam, pp 385–400

Bock VD, Hiemstra H, Van Maarseveen JH (2006) Cu(I)-catalyzed alkyne–azide “click” cycloadditions from a mechanistic and synthetic perspective. Eur J Org Chem 3:51–68CrossRef

Bodin A, Ahrenstedt L, Fink H, Brumer H, Risberg B, Gatenholm P (2007) Modification of nanocellulose with a xyloglucan-RGD conjugate enhances adhesion and proliferation of endothelial cells: implications for tissue engineering. Biomacromolecules 8:3697–3704CrossRef

Chen GJ, Tao L, Mantovani G, Ladmiral V, Burt DP, Macpherson JV, Haddleton DM (2007) Synthesis of azide/alkyne-terminal polymers and application for surface functionalisation through a [2 + 3] Huisgen cycloaddition process, “click chemistry”. Soft Matter 3:732–739CrossRef

Chen ZX, Zhu JT, Xie HB, Li S, Wu YM, Gong YF (2010) Copper(I)-catalyzed synthesis of novel 4-(trifluoromethyl)-[1,2,3]triazolo[1,5-a]quinoxalines via cascade reactions of N-(o-haloaryl)alkynylimine with sodium azide. Adv Synth Catal 352:1296–1300CrossRef

Chen Y, Qian XR, An XH (2011) Preparation and characterization of conductive paper via in situ polymerization of 3,4-ethylenedioxythiophene. BioResources 6:3410–3423

Derikvand F, Yin DT, Barrett R, Brumer H (2016) Cellulose-based biosensors for esterase detection. Anal Chem 88:2989–2993CrossRef

Ding CY, Qian XR, Shen J, An XH (2010) Preparation and characterization of conductive paper via in situ polymerization of pyrrole. BioResources 5:303–315

Elchinger PH, Faugeras PA, Boëns B, Brouillette F, Montplaisir D, Zerrouki R, Lucas R (2011) Polysaccharides: the “click” chemistry impact. Polymers 3:1607–1651CrossRef

Filpponen I, Kontturi E, Nummelin S, Rosilo H, Kolehmainen E, Ikkala O, Laine J (2012) Generic method for modular surface modification of cellulosic materials in aqueous medium by sequential “click” reaction and adsorption. Biomacromolecules 13:736–742CrossRef

Finn MG, Kolb HC, Fokin VV, Sharpless KB (2008) Click chemistry: definition and aims. Prog Chem 20:1–4

Gandini A, Pasquini D (2012) The impact of cellulose fibre surface modification on some physico-chemical properties of the ensuing papers. Ind Crop Prod 35:15–21CrossRef

Grigoray O, Wondraczek H, Heikkila E, Fardim P, Heinze T (2014) Photoresponsive cellulose fibers by surface modification with multifunctional cellulose derivatives. Carbohydr Polym 111:280–287CrossRef

Hafren J, Zou WB, Cordova A (2006) Heterogeneous ‘organoclick’ derivatization of polysaccharides. Macromol Rapid Commun 27:1362–1366CrossRef

Huang W, Huang JJ, Xu CH, Gu SJ, Xu WL (2014) Surface functionalization of cellulose membrane via heterogeneous “click” grafting of zwitterionic sulfobetaine. Polym Bull 71:2559–2569CrossRef

Junka K, Filpponen I, Johansson L-S, Kontturi E, Rojas OJ, Laine J (2014) A method for the heterogeneous modification of nanofibrillar cellulose in aqueous media. Carbohydr Polym 100:107–115CrossRef

Kolb HC, Finn MG, Sharpless KB (2001) Click chemistry: diverse chemical function from a few good reactions. Angew Chem 40:2004–2021CrossRef

Krouit M, Bras J, Belgacem MN (2008) Cellulose surface grafting with polycaprolactone by heterogeneous click-chemistry. Eur Polym J 44:4074–4081CrossRef

Lee DG, Chang VS (1979) Oxidation of hydrocarbons. 9. The oxidation of alkynes by potassium permanganate. J Org Chem 44:2726–2730CrossRef

Lei Y, Qian XR, Shen J, An XH (2012) Integrated reductive/adsorptive detoxification of Cr(VI)-contaminated water by polypyrrole/cellulose fiber composite. Ind Eng Chem Res 51:10408–10415CrossRef

Li J, Qian XR, Wang LJ, An XH (2010) XPS characterization and percolation behavior of polyaniline-coated conductive paper. BioResources 5:712–726

Liebert T, Hansch C, Heinze T (2006) Click chemistry with polysaccharides. Macromol Rapid Commun 27:208–213CrossRef

Liu XY, Qian XR, Shen J, Zhou WP, An XH (2012) An integrated approach for Cr(VI)-detoxification with polyaniline/cellulose fiber composite prepared using hydrogen peroxide as oxidant. Bioresour Technol 124:516–519CrossRef

Ly EB, Bras J, Sadocco P, Belgacem MN, Dufresne A, Thielemans W (2010) Surface functionalization of cellulose by grafting oligoether chains. Mater Chem Phys 120:438–445CrossRef

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. Biomacromolecules 14:254–263CrossRef

Mao H, Wu XN, Qian XR, An XH (2014) Conductivity and flame retardancy of polyaniline-deposited functional cellulosic paper doped with organic sulfonic acids. Cellulose 21:697–704CrossRef

Meng X, Edgar KJ (2016) “Click” reactions in polysaccharide modification. Prog Polym Sci 53:52–85CrossRef

Ogata Y, Sawaki Y, Ohno T (1982) Mechanism for oxidation of phenylacetylenes with peroxymonophosphoric acid. Oxirene as an intermediate inconvertible to ketocarbene. J Am Chem Soc 104:216–219CrossRef

Paquet O, Krouit M, Bras J, Thielemans W, Belgacem MN (2010) Surface modification of cellulose by PCL grafts. Acta Mater 58:792–801CrossRef

Pohl M, Morris GA, Harding SE, Heinze T (2009) Studies on the molecular flexibility of novel dendronized carboxymethyl cellulose derivatives. Eur Polym J 45:1098–1110CrossRef

Roy D, Semsarilar M, Guthrie JT, Perrier S (2009) Cellulose modification by polymer grafting: a review. Chem Soc Rev 38:2046–2064CrossRef

Stejskal J, Gilbert RG (2002) Polyaniline. Preparation of a conducting polymer. Pure Appl Chem 74:857–867CrossRef

Tang JS, Wang LX, Jing XB, Wang FS (1989) The effect of acid concentration on the aniline polymerization and the characterization of polymers obtained. Acta Polym Sin 2:188–191

van Berkel SS, Dirks ATJ, Debets MF, van Delft FL, Cornelissen JJLM, Nolte RJM, Rutjes FPJT (2007) Metal-free triazole formation as a tool for bioconjugation. ChemBioChem 8:1504–1508CrossRef

Xiong FQ, Han YM, Li GY, Qin TF, Wang SQ, Chu FX (2016) Research status of click chemistry used for chemical modification of lignocellulose. Sci Silvae Sin 52:90–96

Xu C, Spadiut O, Silva ACA, Brumer H (2012) Chemo-enzymatic assembly of clickable cellulose surfaces via multivalent polysaccharides. ChemSusChem 5:661–665CrossRef

Yilmaz F, Kucukyavuz Z (2013) The influence of polymerization temperature on structure and properties of polyaniline. E-Polymers 9:48–57

Zampano G, Bertoldo M, Bronco S (2009) Poly(ethyl acrylate) surface-initiated ATRP grafting from wood pulp cellulose fibers. Carbohydr Polym 75:22–31CrossRef

Zhao GL, Hafren J, Deiana L, Cordova A (2010) Heterogeneous “organoclick” derivatization of polysaccharides: photochemical thiol-ene click modification of solid cellulose. Macromol Rapid Commun 31:740–744CrossRef

Zhou Q, Baumann MJ, Brumer H, Teeri TT (2006) The influence of surface chemical composition on the adsorption of xyloglucan to chemical and mechanical pulps. Carbohydr Polym 63:449–458CrossRef

Zhou Q, Rutland MW, Teeri TT, Brumer H (2007) Xyloglucan in cellulose modification. Cellulose 14:625–641CrossRef

Title: Facile strategy for preparation of alkyne-functionalized cellulose fibers with click reactivity
Authors: Guifa Xiao
Chunyue Ding
Feiyu Song
Xueren Qian
Xianhui An
Publication date: 10-12-2016
Publisher: Springer Netherlands
Published in: Cellulose / Issue 2/2017
Print ISSN: 0969-0239
Electronic ISSN: 1572-882X
DOI: https://doi.org/10.1007/s10570-016-1153-1

Springer Professional

Abstract

Please log in to get access to your license.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Technik"

Springer Professional "Wirtschaft+Technik"

Other articles of this Issue 2/2017

Facile cellulose nanofibrils amidation using a ‘one-pot’ approach

Probing the structural chirality of crystalline cellulose with induced circular dichroism

The nanocellulose biorefinery: woody versus herbaceous agricultural wastes for NCC production

Effect of sodium dodecyl sulfate and cetyltrimethylammonium bromide catanionic surfactant on the enzymatic hydrolysis of Avicel and corn stover

Effects of liquid crystalline and shear alignment on the optical properties of cellulose nanocrystal films

Substituent effects on the kinetics of acid-catalyzed hydrolysis of methyl cellulose