Cellulose paper azide as a molecular platform for versatile click ligations: application to the preparation of hydrophobic paper surface

Nongbe, Medy C.; Bretel, Guillaume; Ekou, Lynda; Ekou, Tchirioua; Robitzer, Mike; Grognec, Erwan Le; Felpin, François‐Xavier

doi:10.1007/s10570-017-1647-5

Cited by 25 publications

(13 citation statements)

References 76 publications

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“…We recently described the straightforward preparation of cellulose paper azide (Cell-N 3 ) which results from the azidation of C6-alcohol functions of glucose residues (Nongbe et al, 2018a). Cell-N 3 is obtained in two steps from pristine cellulose with degree of substitution (DS) of ca.…”

Section: Preparation Of the Cellulose Paper-grafted Quininementioning

confidence: 99%

A fully bio-sourced adsorbent of heavy metals in water fabricated by immobilization of quinine on cellulose paper

Aka

Nongbe

Ekou

et al. 2019

Journal of Environmental Sciences

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The fabrication of a fully bio-sourced adsorbent of Cd(II) by covalent immobilization of quinine on cellulose paper is described. The double bond of commercially available quinine was converted to a terminal alkyne function which was reacted with cellulose paper, chemically modified with azide functions, through a 1,3-dipolar cycloaddition, leading to Cell-Quin. The adsorption efficiency of Cell-Quin was investigated to determine the optimal pH, contact time and dose of adsorbent, ultimately leading to high levels of removal. The mechanism of adsorption of Cell-Quin was deeply rationalized through kinetic experiments and isotherm modeling. We also showed that Cell-Quin could adsorb other heavy metals such as Cu(II), Pb(II), Ni(II) and Zn (II).

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Section: Preparation Of the Cellulose Paper-grafted Quininementioning

confidence: 99%

A fully bio-sourced adsorbent of heavy metals in water fabricated by immobilization of quinine on cellulose paper

Aka

Nongbe

Ekou

et al. 2019

Journal of Environmental Sciences

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“…However, due to the high hydrophilicity of the NCC polyhydroxyl groups, they readily agglomerate in the PLA matrix, and hence the surface hydrophobic modification of NCC was typically performed [25]. Modification techniques that were often utilized included physical adsorption modification [26][27][28][29], esterification modification properties [30][31][32][33], graft copolymerization [34][35][36][37], and silane coupling agent modification [38][39][40][41]. e modified NCC could be more uniformly dispersed in the polymer matrix and played an effective role as nanoparticles.…”

Section: Introductionmentioning

confidence: 99%

Preparation and Supercritical CO2 Foaming of Modified Nanocrystalline Cellulose Reinforced Polylactic Acid Bionanocomposites

Chen

Zhang

Wang

et al. 2022

Advances in Materials Science and Engineering

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The solution casting method was used to prepare polylactic acid/modified nanocrystalline cellulose (PLA/mNCC) composites, and the effects of the mNCC content on the morphology, thermal characteristics, and rheological properties of the PLA nanocomposite were examined. The PLA microcellular foaming nanocomposite was prepared using supercritical CO2 foaming. Furthermore, the foaming conditions were optimized, and the effect of NCC surface modification, as well as the content and interfacial force of nanoparticles, on the foaming efficiency and cell pattern of composites was examined. The results suggested that a sufficient number of nanoparticles increased the nucleation site for foaming and played a vital role in heterogeneous nucleation in the foaming system. An ideal microcellular foaming material with an average cell diameter of 6.97 μm and a cell density of 6.05 × 109 cells/cm3 was prepared when the foaming temperature was 110°C, the foaming pressure was 18 MPa, the incubation period was 2 h, and the mNCC content was 6%.

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“…Moreover, azide group containing cellulose derivative could be crosslinked with propargyl modified cyclodextrin to obtain biocompatible gels . The surface of cellulose fibers was modified as well, for example, by copolymerization of alkyne‐containing monomers, by silane chemistry, or by tosylation of the paper surface followed by nucleophilic displacement with azide ions . The functionalities attached can possess photomicrobicidal properties or increase the strength of pulp fibers .…”

Section: Introductionmentioning

confidence: 99%

All Sugar Based Cellulose Derivatives Synthesized by Azide–Alkyne Click Chemistry

Koschella

Chien

Iwata

et al. 2019

Macro Chemistry & Physics

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chemically by, for example, glycosylation reactions. [3,4] Cellulose can be converted to the corresponding orthoesters by reaction with acetobromoglucose in presence of triethylamine. [5] However, the methods described so far require the use of hazardous reagents. The copper-catalyzed azide-alkyne cycloaddition was found to be advantageous for the preparation of numerous cellulose derivatives. [6,7] This reaction proceeds under mild conditions and even in aqueous media. In addition to a proof of principle, for example, [8,9] this type of click reaction has been utilized for the synthesis of highlyengineered cellulose derivatives. Dendron-like moieties could be attached to cellulose, [10] where either the azide [11] or the alkyne moiety was attached to the complementarily modified polymer backbone. [12] Moreover, azide group containing cellulose derivative could be crosslinked with propargyl modified cyclodextrin to obtain biocompatible gels. [13] The surface of cellulose fibers was modified as well, for example, by copoly merization of alkyne-containing monomers, [14] by silane chemistry, [15,16] or by tosylation of the paper surface followed by nucleophilic displacement with azide ions. [17] The functionalities attached can possess photomicrobicidal properties [18-20] or increase the strength of pulp fibers. [21] Maltose derivatives bearing N-and O-linked propargyl moieties attached to cellulose by azide-alkyne click chemistry increase the water solubility of the polymer. [22,23] This approach of click chemistry enabled the preparation of cellulose block copolymers by using cellulose derivatives bearing alkyne-or azide groups at position 1 of the reducing end of the oligosaccharide chain. [24] The reactive groups can be introduced regioselectively by, for example, 3-O-azidopropoxypoly(ethylene glycol)-2,6-di-O-thexyldimethylsilyl cellulose [25] or 3-O-propargyl cellulose. [26] In the context of plastic waste including the micro-plastic problems, biobased and biodegradable polymers are highly desirable. In this respect, solubility is an interesting parameter to enhance the biocompability of polymers. Moreover, functional polymers synthesized completely based on renewable resource (polymeric and monomeric carbohydrates) are important in order to save fossil resources. In the present paper the synthesis and structural characterization of cellulose derivatives bearing sugar moieties is reported that impart solubility to the polymer by taking advantages of the click chemistry approach. Cellulose is functionalized with different monosaccharides by the azide-alkyne click chemistry approach. Either azide or alkyne moieties are attached to the cellulose backbone and allowed to react with sugar moieties bearing the opposite clickable groups. Between 16% and 100% of the reactive sites at the polymer can be functionalized with sugar molecules and a clear correlation between steric demand and DS Sugar is observed. The polymers remain soluble in aprotic dipolar media like dimethyl sulfoxide. Products with a sufficient hydroph...

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Cellulose paper azide as a molecular platform for versatile click ligations: application to the preparation of hydrophobic paper surface

Cited by 25 publications

References 76 publications

A fully bio-sourced adsorbent of heavy metals in water fabricated by immobilization of quinine on cellulose paper

A fully bio-sourced adsorbent of heavy metals in water fabricated by immobilization of quinine on cellulose paper

Preparation and Supercritical CO2 Foaming of Modified Nanocrystalline Cellulose Reinforced Polylactic Acid Bionanocomposites

All Sugar Based Cellulose Derivatives Synthesized by Azide–Alkyne Click Chemistry

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