Novel cellulose-based polyelectrolytes synthesized via the click reaction

Koschella, Andreas; Richter, Martin; Heinze, Thomas

doi:10.1016/j.carres.2010.03.007

Cited by 17 publications

(6 citation statements)

References 18 publications

(12 reference statements)

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“…The copper-catalyzed azidealkyne cycloaddition (CuAAC) is one of the most used ''click''-reaction employed in polymer synthesis, offering extensive possibilities to tailor polymer properties Sachsenhofer 2007, 2008;Fournier et al 2007;Meldal 2008;Rostovtsev et al 2002;Tornoe et al 2002). Click-chemistry has also gained attention in the modification of polysaccharides and several articles on the topic can be found (Bernard et al 2008;De Geest et al 2008a, b;Hafrén et al 2006;Hasegawa et al 2006;Koschella et al 2010;Krouit et al 2008;Liebert et al 2006;Schatz et al 2009;Tankam et al 2007;Zhang et al 2009;Zhao et al 2010).…”

Section: Introductionmentioning

confidence: 99%

Surface functionalization of nanofibrillated cellulose using click-chemistry approach in aqueous media

et al. 2011

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In the present work, amino functionalized nanofibrillated cellulose (NFC) was prepared using click-chemistry in aqueous reaction conditions. First, reactive azide groups were introduced on the surface of NFC by the etherification of 1-azido-2,3-epoxypropane in alkaline water/isopropanol-mixture at ambient temperature. Then the azide groups were reacted with propargyl amine utilizing copper catalyzed azide-alkyne cycloaddition (CuAAC), leading to pH-responsive 1,2,3-triazole-4-methanamine decorated NFC. The reaction products were characterized using Fourier transform infrared spectroscopy, elemental analysis and X-ray photoelectron spectroscopy. The presence of the attached azide groups was also confirmed by reacting them with 5-(dimethylamino)-N-(2-propyl)-1-naphthalenesulfonamide by CuAAC, yielding highly fluorescent NFC. In addition, atom force microscopy and rheology studies confirmed that the original NFC nanostructure was maintained during the synthesis.

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Section: Introductionmentioning

confidence: 99%

Surface functionalization of nanofibrillated cellulose using click-chemistry approach in aqueous media

et al. 2011

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“…Another promising approach for synthesis of cationic or basic cellulose derivatives having N-functions is the introduction of an appropriate moiety (azide or carboncarbon triple bond) into cellulose by S N reaction and subsequent Huisgen cycloaddition as a click reaction. [26,[77][78][79][80][81][82][83] Huisgen reaction is a 1,3-dipolar cycloaddition between an azide and a terminal or internal alkyne to give a 1,2,3-triazole. Because of its simplicity, high selectivity, and nearly quantitative yields, this reaction has rapidly become the most popular click reaction to date.…”

Section: Methodsmentioning

confidence: 99%

“…Another promising approach for synthesis of cationic or basic cellulose derivatives having N ‐functions is the introduction of an appropriate moiety (azide or carbon–carbon triple bond) into cellulose by S N reaction and subsequent Huisgen cycloaddition as a click reaction . Huisgen reaction is a 1,3‐dipolar cycloaddition between an azide and a terminal or internal alkyne to give a 1,2,3‐triazole.…”

Section: Synthesis Of N‐functionalized Basic and Cationic Cellulose Dmentioning

confidence: 99%

“…The key reaction in this synthesis was the conversion of an azide‐containing cellulose derivative with compounds bearing an alkyne moiety via the copper‐catalyzed Huisgen reaction (click reaction) that affords multifunctional, regioselective cellulose products without structural impurities. Various derivatives have been synthesized using this strategy (Scheme ) …”

Section: Synthesis Of N‐functionalized Basic and Cationic Cellulose Dmentioning

confidence: 99%

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Designing syntheses of cellulose and starch derivatives with basic or cationic N‐functions: part I—cellulose derivatives

Satha

Aryanasab

Banazadeh

et al. 2015

Polymers for Advanced Techs

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The use of cellulose and starch derivatives that bear amino or quaternary ammonium moieties is steadily increasing, and the applications in industry are continuing to grow. These promising products are routinely used in cosmetic and paper‐making industries. This article provides an overview of strategies available to chemists for designing the syntheses of such compounds. The review provides a brief historical perspective on synthesis and describes recent developments that have enabled chemists to enhance their synthesis productivity. However, the graft polymerization techniques are far from the scope of this paper and will be noted in a few words only. In addition to the structural and synthetic aspects, applications of these derivatives are discussed in brief. We have divided this article in two parts mainly because of the vastness of the subject and limited space available. The first part of which reviews the advances in the synthesis of basic and cationic cellulose derivatives having amino or quaternary ammonium moieties and the second part of which considers starch ones. Copyright © 2015 John Wiley & Sons, Ltd.

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“…16 In the course of our ongoing work on water-soluble cellulose derivatives, we have reported results on oxidized cellulose derivatives 17 , cellulosics bearing cationically charged moieties, 18 cellulosics bearing oxocarbonic acid esters of high DS, 19 carboxymethyl cellulose 20 , and cellulose polyelectrolytes prepared via click-reaction. 21 For homogeneous chemical modification of cellulose, DMA/LiCl developed by McCormick, is a very versatile reaction medium. 22 Moreover, ionic liquids (IL) gained increasing interest in carbohydrate chemistry, 23 in particular for esterification [24][25][26] and etherification.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of branched polysaccharides by reaction of cellulose with 2,3,4,6-tetraacetyl-1-bromo-α-D-glucopyranoside

Koschella¹,

Dorn²,

Heinze³

et al. 2012

Arkivoc

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Non-naturally branched polysaccharides were prepared homogeneously by reaction of cellulose in N,N-dimethyl acetamide/LiCl and the ionic liquid 1-N-butyl-3-methylimidazolium chloride with 2,3,4,6-tetraacetyl-1-bromo-α-D-glucopyranoside in the presence of triethylamine as base. Degrees of substitution up to 0.58 were realized. The samples were soluble in dimethyl sulphoxide and water. NMR spectroscopy and methylation analysis revealed the formation of 1,2-orthoesters. The purity of the products regarding non-bonded sugar molecules was evidenced by advanced NMR techniques (DOSY-and T 2 measurements). In contrast to the reaction in 1-N-butyl-3-methylimidazolium chloride, 1-N-ethyl-3-methylimidazolium acetate acts not only as solvent but also as reagent and leads to the formation of cellulose acetate instead of the desired product.

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Novel cellulose-based polyelectrolytes synthesized via the click reaction

Cited by 17 publications

References 18 publications

Surface functionalization of nanofibrillated cellulose using click-chemistry approach in aqueous media

Surface functionalization of nanofibrillated cellulose using click-chemistry approach in aqueous media

Designing syntheses of cellulose and starch derivatives with basic or cationic N‐functions: part I—cellulose derivatives

Synthesis and characterization of branched polysaccharides by reaction of cellulose with 2,3,4,6-tetraacetyl-1-bromo-α-D-glucopyranoside

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