1246216-23-8Relevant articles and documents
Diazirine-modified gold nanoparticle: Template for efficient photoinduced interfacial carbene insertion reactions
Ismaili, Hossein,Lee, Soo,Workentin, Mark S.
, p. 14958 - 14964 (2011/10/31)
Photolysis of a 3-aryl-3-(trifluoromethyl)diazirine-modified monolayer-protected gold nanoparticles (2-C12MPNs), with a core size of 1.8 ± 0.3 nm, in the presence of model carbene trapping reagents leads to efficient, essentially quantitative, modification of the interface via carbene insertion reactions. The utility of carbene insertion reactions as a general approach for the modification of Au-MPNs to provide a breadth of new structures available was demonstrated using acetic acid, methanol, benzyl alcohol, phenol, benzylamine, methyl acrylate, and styrene (10a-g, respectively) as electrophilic carbene trapping agents to form the corresponding modified 3a-g-C12MPNs. The 1.8 ± 0.3 nm gold nanoparticles bearing a diazirine group (2-C12MPNs) were synthesized using the ligand exchange reaction with the requisite 3-aryl-3-(trifluoromethyl) diazirinealkylthiol. The 2-C12MPNs and the resulting products of the reaction on the MPN (3a-g-C12MPN) were fully characterized by IR, 1H NMR, and 19F NMR spectroscopy and, when applicable, transmission electron microscopy (TEM). Verification for the 3a-g-C 12MPNs was accomplished by comparison of the spectral data to those of obtained for the photoreactions of 3-(3-methoxyphenyl)-3-(trifluoromethyl)- 3H-diazirine as a model with 10a-g.
