Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 354, Issue 6, Pages 1001-1011Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201100865
Keywords
alkynes; azides; click chemistry; copper catalysts; dendrimers; gold nanoparticles; polymers
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Funding
- China Scholarship Council (CSC) from the People's Republic of China
- Universite Bordeaux 1
- Centre National de la Recherche Scientifique (CNRS)
- Agence Nationale de la Recherche (ANR)
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Whereas previous click functionalization (Huisgen-type copper-catalyzed alkyne-azide cycloaddition, CuAAC) of various gold nanoparticles (AuNP) had systematically proven to be very difficult, tedious, providing low yields with the use of high amounts of copper sulfate+sodium ascorbate the classic Sharpless catalyst, the new catalyst copper(I) (hexabenzyl)tris(2-aminoethyl)amine bromide, {[Cu(I)(Hexabenzyl)Tren]Br} is shown here to be very efficient for the introduction of a large variety of organic, organometallic, dendronic and polymeric molecular fragments of various sizes, topologies and hydrophilicities. Indeed, 0.10.15 equiv. of this catalyst in toluene was used in each reaction under ambient conditions for 8 to 48 h with good yields without AuNP aggregation. The new functional AuNP have been characterized by 1H NMR, IR and UV-vis. (plasmon band) spectroscopy, cyclic voltammetry (CV), dynamic light scattering (DLS) and transmission electron microscopy (TEM).
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