Interfacial ketene via the photo‐Wolff rearrangement for the modification of monolayer protected gold nanoparticles. (29th May 2013)

• Record Type: Journal Article
• Authors: Snell, Kristen E.; Johnson, Michel; Hesari, Mahdi; Ismaili, Hossein; Workentin, Mark S.
• Is Part Of: Journal of physical organic chemistry. Volume 26:Number 7(2013:Jul.)
• Page Start: 601
• Page End: 607
• Publication Date: 2013-05-29
• Subjects: Chemistry, Physical organic -- Periodicals; 547.1
• DOI: 10.1002/poc.3139
• Languages: English
• ISSNs: 0894-3230

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>An interfacial diazoketone‐modified gold nanoparticle (AuNP) was prepared and characterized by ¹H NMR and IR spectroscopy, TGA and TEM. Irradiation of the diazoketone leads to loss of nitrogen and the formation an interfacial ketene–AuNP via the photo‐Wolff <named-content id="d144e617" content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">rearrangement</named-content>, evidenced by the loss of the characteristic C = N = N signal at 2068 cm⁻¹ in the IR spectrum and the growth of a new signal at 2100 cm⁻¹ indicative of the ketene. This ketene is relatively stable in the absence of added nucleophiles, but reacts quickly with oxygen nucleophiles illustrating the potential use of this ketene–AuNP as a template for a wide range of <named-content id="d144e626" content-type="chemicalTechnology" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">surface modifications</named-content>. Copyright © 2013 John Wiley &amp; Sons, Ltd.</p> </abstract>