Synthesis of Dendrimers Through Divergent Iterative Thio-Bromo "Click" Chemistry

被引：210

作者：

Rosen, Brad M. ^{[1
]}

Lligadas, Gerard ^{[1
]}

Hahn, Christian ^{[1
]}

Percec, Virgil ^{[1
]}

机构：

[1] Univ Penn, Roy & Diana Vagelos Labs, Dept Chem, Philadelphia, PA 19104 USA

来源：

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY | 2009年 / 47卷 / 15期

基金：

美国国家科学基金会;

关键词：

branched; click chemistry; dendrimers; synthesis; LIVING RADICAL POLYMERIZATION; SELF-ASSEMBLING DENDRONS; TAPER-SHAPED MONOESTERS; CONSTITUTIONAL ISOMERIC AB(2); SET-LRP; DENDRITIC MACROMOLECULES; LIQUID-CRYSTALLINE; SUPRAMOLECULAR ARCHITECTURES; METHYL ACRYLATE; STRUCTURAL-ANALYSIS;

D O I：

10.1002/pola.23519

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 development of a novel nucleophilic thio-bromo "Click" reaction, specifically base-mediated thioetherification of thioglycerol with alpha-bromoesters, is reported. Combination of this thio-bromo click reaction with subsequent acylation with 2-bromopropionyl bromide provides an iterative two-step divergent growth approach to the synthesis of a new class of poly(thioglycerol-2-propionate) (PTP) dendrimers. This approach is demonstrated in the rapid preparation of four generation (G1-G4) of PTP dendrimers with high-structural fidelity. The isolated G1-G4 bromide-terminated dendrimers can be used directly as dendritic macroinitiators for the synthesis of star-polymers via SET-LRP. Additionally, the intermediate hydroxy-terminated dendrimers are analogs of other water-soluble polyester and polyether dendrimers. (C) 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 3931-3939, 2009

引用

页码：3931 / 3939

页数：9

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