Multiblock sequence-controlled glycopolymers via Cu(0)-LRP following efficient thiol-halogen, thiol-epoxy and CuAAC reactions
Multiblock sequence-controlled glycopolymers via Cu(0)-LRP following efficient thiol-halogen, thiol-epoxy and CuAAC reactions
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DOI：
10.1039/c4py00320a
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发表时间：
2014-05
影响因子：
4.6
通讯作者：
Qiang Zhang;Athina Anastasaki;Guang-Zhao Li;Alice J. Haddleton;P. Wilson;D. Haddleton
中科院分区：
文献类型：
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作者：
Qiang Zhang;Athina Anastasaki;Guang-Zhao Li;Alice J. Haddleton;P. Wilson;D. Haddleton
将铜（0）介导的活性自由基聚合（Cu（0）-LRP）与硫醇-卤素、硫醇-环氧和铜催化的炔叠氮偶联（CuAAC）点击化学相结合，得到了一种新的多嵌段序列控制的糖基共聚物的合成方法。通过Cu（0）-LRP在DMSO中在环境温度下通过重复单体添加获得多嵌段聚（丙烯酸缩水甘油酯）-co-（丙烯酸3-三甲基硅烷基-丙-2-炔基酯）（聚（GA）-co-（TMSPA）），由此以设计的方式获得多嵌段序列。利用三乙胺作为催化剂，研究了聚（GA）的硫醇-卤素反应和硫醇-环氧反应，结果表明硫醇的卤素反应优于环氧反应。然后将得到的多嵌段聚（GA）-co-（TMSPA）用于顺序的硫醇-卤素、硫醇-环氧和CuAAC反应以按定义的顺序构建功能性糖共聚物。
The combination of copper(0) mediated living radical polymerization (Cu(0)-LRP) with thiol–halogen, thiol–epoxy and copper catalysed alkyne azide coupling (CuAAC) click chemistry has been employed to give a new route to multiblock sequence-controlled glycopolymers. Multiblock poly(glycidyl acrylate)-co-(acrylic acid 3-trimethylsilanyl-prop-2-ynyl ester) (poly(GA)-co-(TMSPA)) were obtained by Cu(0)-LRP in DMSO at ambient temperature via iterative monomer addition whereby the sequence of the multi blocks is attained in a designed way. Thiol–halogen and thiol–epoxy reaction of poly(GA) have been exploited, which suggested a preference for the reaction of the halogen rather than the epoxide for the thiol with triethyl amine as catalyst. The obtained multiblock poly(GA)-co-(TMSPA) were then used for sequential thiol–halogen, thiol–epoxy and CuAAC reactions to build functional glycopolymers in defined sequence.