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

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.