Water-Soluble Maleimide-Modified Gold Nanoparticles (AuNPs) as a Platform for Cycloaddition Reactions

作者：Ghiassian Sara; Gobbo Pierangelo; Workentin Mark S^*

来源：European Journal of Organic Chemistry, 2015, 2015(24): 5438-5447.

DOI：10.1002/ejoc.201500685

• Nanoparticles
• Gold
• Cycloaddition
• Water chemistry

Maleimide-terminated triethylene glycol thiolate monolayer-protected gold nanoparticles (Mal-EG(4)-AuNPs) with a core size of 2.5 +/- 0.7 nm were prepared. Mal-EG(4)-AuNPs were modified in high yields via interfacial 1,3-dipolar cycloaddition and Diels-Alder reactions with a variety of nitrones and dienes, respectively. The resulting cycloadduct-modified AuNPs were characterized using H-1 NMR spectroscopy and were verified by comparison of the spectra to those of the products of the model reactions with the same nitrones and dienes. TEM analysis showed that the reaction conditions did not affect the shape or size of the gold core, suggesting that this is an efficient methodology to modify small water soluble AuNPs under ambient pressure and biological temperature with high yields and a reasonable reaction time.

• 出版日期2015-8