鈥淐lick鈥?Synthesis of Intrinsically Hydrophilic Dendrons and Dendrimers Containing Metal Binding Moieties at Each Branching Unit

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• 作者：Lili Wang ; David J. Kiemle ; Connor J. Boyle ; Eoghan L. Connors ; Ivan Gitsov
• 刊名：Macromolecules
• 出版年：2014
• 出版时间：April 8, 2014
• 年：2014
• 卷：47
• 期：7
• 页码：2199-2213
• 全文大小：756K
• 年卷期：v.47,no.7(April 8, 2014)
• ISSN：1520-5835

文摘

A new family of water-soluble triazole dendrimers composed of tri(ethylene glycol) (TrEG) and bis(methylol)propionic acid (bis-MPA) was created through Cu(I)-catalyzed alkyne鈥揳zide cycloaddition (CuAAC) between specifically designed complementary building blocks. Dendrimers up to generation three were synthesized by CuAAC to a trifunctional core with yields ranging from 72% for generation one, through 67% for generation two, and 64% for third generation dendrimer. The two triazole rings at each bis-MPA branching site could serve as efficient chelating pockets for some VIIIA group elements. As proof-of-principle, the [PdCl₂(PhCN)₂] coordination chemistry of these hydrophilic dendritic ligands was studied by ¹H NMR, dynamic light scattering, transmission electron microscopy, and DFT calculations. The results showed that the complexation is completed within 5 min. The novel hydrophilic dendritic Pd complexes were able to catalyze Suzuki鈥揗iyaura coupling reactions in water within 3 h at 100 掳C, at 60 掳C, and even at 50 掳C with practically quantitative conversion.