Cellulose fibers modification through metal-free click chemistry for the elaboration of versatile functional surfaces. (15th July 2020)

• Record Type: Journal Article
• Authors: Meye Biyogo, Alex; Hespel, Louise; Humblot, Vincent; Lebrun, Laurent; Estour, François
• Is Part Of: European polymer journal. Volume 135(2020)
• Publication Date: 2020-07-15
• Subjects: Cellulose functionalization -- β-cyclodextrin -- Metal-free click chemistry; Polymers -- Periodicals; Polymerization -- Periodicals; Polymères -- Périodiques; Polymérisation -- Périodiques; Polymerization; Polymers; Periodicals; Electronic journals; 547.705
• DOI: 10.1016/j.eurpolymj.2020.109866
• Languages: English
• ISSNs: 0014-3057

Abstract

Graphical abstract: Highlights: Heterogenous « click » reaction without metal on cellulose. Activation of the surface of cellulose with bicyclononyne group. XPS analysis highlight the substitution degree at the surface of cellulose. Abstract: In the present work, a novel and versatile way was developed to functionalize cellulose fibers from wipes under heterogeneous conditions. The technic was based on metal-free click chemistry to avoid the persistence of any metal traces on cellulose. First, cellulose fibers were covalently pre-functionalized with bicyclononyne (BCN) to promoted azide-alkyne addition with molecules of interest, like coumarin and β-cyclodextrin derivatives. X-ray photoelectron microscopy (XPS) shows that one BCN group per cellulose unit was modified at the surface of the wipe. 3-azido-7-hydroxycoumarin that can be used as fluorophore for bio-sensoring applications was efficiently bound to the pre-functionalized cellulose with a yield of reaction estimated at 60%. The addition of 6-azido-per-6-deoxy-β-cyclodextrin (β-CD derivative) was investigated in order to target future organophosphorus decontamination properties to cellulose wipes. With the best reaction conditions, 60% of triazole groups corresponding to 4 reactive azido groups per β-CD derivative were detected by XPS proving the efficiency of the click reaction. The highest DS values were obtained after 96 h for β-CD 20 Eq (DS = 1.7% by elementary analysis and DS = 2.5% by weight measurements). Scanning electron microscopy observations highlighted a globally well distributed β-CD with some aggregates on the surface of the fibers. Thus, the pre-functionalized BCN-cellulose fibers could be used for many applications after an easy clicking of target compounds.