Stereocontrolled Sequence-Defined Oligotriazoles through Metal-Free Elongation Strategies

被引：13

作者：

Wang, Xiaojun ^{[1
]}

Zhang, Xueyan ^{[1
]}

Sun, Yunxin ^{[1
]}

Ding, Shengtao ^{[1
]}

机构：

[1] Beijing Univ Chem Technol, Coll Chem Engn, State Key Lab Organ Inorgan Composites, Beijing 100029, Peoples R China

来源：

MACROMOLECULES | 2021年 / 54卷 / 20期

基金：

中国国家自然科学基金;

关键词：

ITERATIVE EXPONENTIAL-GROWTH; SOLID-PHASE SYNTHESIS; GAMMA-AAPEPTIDES; OLIGOMERS; FOLDAMERS; POLYMERS; UNIFORM; DESIGN;

D O I：

10.1021/acs.macromol.1c01371

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 functionality of biomacromolecules has stimulated the development of stereocontrolled biomimetic oligomers for diverse functional applications. Here we report the synthesis of one novel sequence-defined oligotriazole architecture with excellent stereoregularity from 1,2,3-triazole-based chiral monomers. The facile introduction of broad side chains into this skeleton is enabled by the easy preparation of these building blocks from the efficient reaction of one L-prolinol-derived azide with various internal 1-thioalkynes under mild iridium-catalyzed azide-alkyne cyclo-addition (IrAAC) conditions. Assembly of them into desired oligomers could be achieved through metal-free iterative sequential or exponential growth strategies, the efficiency of which was demonstrated by the construction of three stereocontrolled oligotriazoles bearing different chain lengths and side groups. The structure and monodispersity of these oligomers were well characterized by H-1 NMR, SEC, MS, and tandem MS/MS analysis, and their stereoregularity was identified by circular dichroism.

引用

页码：9437 / 9444

页数：8

共 44 条

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