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

被引:206
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
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
收藏
页码:3931 / 3939
页数:9
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