title: A versatile pathway to end-functionalized cellulose ethers for click chemistry applications.
abstract: This paper describes a versatile pathway to heterobifunctional/telechelic cellulose ethers, such as tri-O-methyl cellulosyl azide and propargyl tri-O-methyl celluloside, having one free C-4 hydroxyl group attached to the glucosyl residue at the non-reducing end for the use in Huisgen 1,3-dipolar cycloaddition and copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC). The one-step end-functionalization of cellulose ethers for molecular rod synthesis involves the introduction of two reactive groups at both ends of the cellulose molecule, and can afford linear triblock copolymers via CuAAC and further reactions. We were able to tailor the degree of polymerization of end-functionalized cellulose ethers with controlled amounts of a Lewis acid, namely SnCl4. Chemical structures of the above cellulose ethers and the reaction conditions for controlling molecular length are discussed.
authors.affiliation: Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan. Electronic address: hkamitan@kais.kyoto-u.ac.jp.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Kamitakahara
authors.affiliation: Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan.
authors.forename: Ryo
authors.initials: R
authors.lastname: Suhara
authors.affiliation: Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan.
authors.forename: Mao
authors.initials: M
authors.lastname: Yamagami
authors.affiliation: Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan.
authors.forename: Haruko
authors.initials: H
authors.lastname: Kawano
authors.affiliation: Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan.
authors.forename: Ryoko
authors.initials: R
authors.lastname: Okanishi
authors.affiliation: Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan.
authors.forename: Tomoyuki
authors.initials: T
authors.lastname: Asahi
authors.affiliation: Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan.
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Takano
mesh_terms: D001386:Azides / Q000737:chemistry*; D002482:Cellulose / Q000737:chemistry*; D057930:Click Chemistry; D004987:Ethers / Q000737:chemistry*
chemical_list: D001386:Azides; D004987:Ethers; D002482:Cellulose
keywords: Copper(I)-catalyzed azide-alkyne cycloaddition; End-functionalized cellulose ether; Functional molecular rod; Propargyl tri-O-methyl celluloside; Tri-O-methyl cellulosyl azide