Structurally diverse dendritic libraries: A highly efficient functionalization approach using Click chemistry

被引:344
作者
Malkoch, M
Schleicher, K
Drockenmuller, E
Hawker, CJ
Russell, TP
Wu, P
Fokin, VV
机构
[1] IBM Corp, Almaden Res Ctr, San Jose, CA 95120 USA
[2] Univ Massachusetts, Dept Polymer Sci & Engn, Amherst, MA 01003 USA
[3] Univ Calif Santa Barbara, Dept Chem, Santa Barbara, CA 93106 USA
[4] Univ Calif Santa Barbara, Dept Mat, Santa Barbara, CA 93106 USA
[5] Univ Calif Santa Barbara, Mat Res Lab, Santa Barbara, CA 93106 USA
[6] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[7] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
关键词
D O I
10.1021/ma047657f
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
The high fidelity and efficiency of Click chemistry are exploited in the synthesis of a library of chain end functionalized dendritic macromolecules. In this example, the selectivity of the Cu-catalyzed [3 + 2 pi] cycloaddition reaction of azides with terminal acetylenes, coupled with mild reaction conditions, permits unprecedented functional group tolerance during the derivatization of dendrimeric and hyperbranched scaffolds. The resulting dendritic libraries are structurally diverse, encompassing a variety of backbones/surface functional groups, and are prepared in almost quantitative yields under very mild conditions. The robust and simple nature of this procedure, combined with its applicability to many aspects of polymer synthesis and materials chemistry, demonstrates an evolving synergy between advanced organic chemistry and functional materials.
引用
收藏
页码:3663 / 3678
页数:16
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