Facile functionalization of gold nanoparticles via microwave-assisted 1,3 dipolar cycloaddition.
This contribution describes a simple and facile method for the functionalization of thiol-coated gold nanoparticles using microwave-assisted 1,3 dipolar cycloadditions. The developed procedure allows for the attachment of terminal alkynes onto azide-containing gold nanoparticles in nearly quantitative conversions within minutes. The utility of the method has been demonstrated by attaching a library of substituted alkynes onto gold nanoparticles in nearly quantitative yields. In a proof of principle study, we demonstrate the potential use of this methodology in catalysis by attaching palladium catalysts to the azide-containing gold nanoparticles and investigate the resulting materials as supported catalysts in Suzuki couplings. Activities that rival the nonsupported analogues were observed, demonstrating that the nanoparticle support does not interfere with the catalytic activity.
Sommer
William J
WJ
School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA 30332, USA.
Weck
Marcus
M
D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D053768:Metal Nanoparticles / Q000737:chemistry*; D008872:Microwaves; D010165:Palladium / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry
D000480:Alkynes; D001386:Azides; D006571:Heterocyclic Compounds; D013438:Sulfhydryl Compounds; D010165:Palladium; D006046:Gold