Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan.
Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan.
Carbohydr Polym. 2016 Oct 20;151:88-95. doi: 10.1016/j.carbpol.2016.05.016. Epub 2016 May 16.
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.
本文描述了一种通用的途径，可将异双官能/遥爪纤维素醚（如三-O-甲基纤维素叠氮化物和炔丙基三-O-甲基纤维素）转化为具有一个游离 C-4 羟基的化合物，该羟基连接在非还原端的葡萄糖基残基上，用于 Huisgen 1,3-偶极环加成和铜（I）-催化的叠氮化物-炔烃环加成（CuAAC）反应。纤维素醚的一步端官能化用于分子棒合成，涉及在纤维素分子的两端引入两个反应性基团，并可通过 CuAAC 和进一步的反应提供线性三嵌段共聚物。我们能够通过控制路易斯酸 SnCl4 的用量来调整端官能化纤维素醚的聚合度。讨论了上述纤维素醚的化学结构和控制分子长度的反应条件。
