Efficient synthesis of isoxazolidine-tethered monolayer-protected gold nanoparticles (MPGNs) via 1,3-dipolar cycloadditions under high-pressure conditions

The Journal of Organic Chemistry
Jun ZhuMark S Workentin

Abstract

A maleimide-modified 2.5 +/- 0.5 nm mixed monolayer protected gold nanoparticle (2-C(12)MPGN) containing approximately 30% maleimide-terminated dodecanethiolate/dodecanethiolate ligands was prepared. The 2-C(12)MPGN was reacted with a series of nitrones (a-i) at both atmospheric and hyperbaric (11 000 atm) conditions to form the corresponding isoxazolidine-modified nanoparticles (3-C(12)MPGN) via an interfacial 1,3-dipolar cycloaddition. At atmospheric pressures, the reaction proceeds slowly (if at all) and makes this reaction impractical for the synthetic modification of the nanoparticles. However, by performing the reaction under the high-pressure conditions, the reaction proceeds efficiently and quantitatively. TEM shows that the use of high pressure does not affect the size of the gold nanoparticle core. The 3-C(12)MPGNs were characterized by (1)H NMR spectroscopy by comparing the spectra obtained with those of model reactions utilizing N-dodecylmaleimide (4) with the same nitrones (a-i) to form 5. Additionally, the cycloaddition reaction also occurs more readily with 4 than with 2-C(12)MPGN with all nitrones, indicating that the environment of the latter affects the cycloaddition reaction.

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Citations

Mar 20, 2015·Organic & Biomolecular Chemistry·Pierangelo GobboMark S Workentin
Mar 2, 2018·Chemistry : a European Journal·Rafael R CastilloMaría Vallet-Regí
Jun 24, 2010·Chemistry : a European Journal·Jocelyn J TindalePaul J Ragogna
Jan 30, 2010·Chemical Society Reviews·Marie Kissane, Anita R Maguire
May 17, 2008·Langmuir : the ACS Journal of Surfaces and Colloids·Christopher J Thode, Mary Elizabeth Williams
Sep 2, 2008·Langmuir : the ACS Journal of Surfaces and Colloids·Xiaofeng LiuYuliang Li
Dec 24, 2009·Langmuir : the ACS Journal of Surfaces and Colloids·Xiaofeng LiuAndong Xia
Aug 26, 2010·Langmuir : the ACS Journal of Surfaces and Colloids·Hossein IsmailiMark S Workentin
Aug 14, 2012·Langmuir : the ACS Journal of Surfaces and Colloids·Pierangelo Gobbo, Mark S Workentin
Mar 21, 2012·Langmuir : the ACS Journal of Surfaces and Colloids·Jun ZhuRalf Schirrmacher
Nov 17, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Kurtis D HartlenMark S Workentin

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