Multidentate Ionic Surfactant Mediated Extraction and Dispersion of Gold Nanoparticles in Organic Solvents

Resorcinarenes with three different quaternary ammonium headgroups were synthesized and evaluated for their ability to stabilize gold nanoparticles in organic and aqueous medium. Aqueous dispersions of citrate stabilized gold nanoparticles of dimensions up to 29 nm could be extracted into organic solvents by resorcinarenes functionalized with tetrapyridinium tetrabromide (1), tetratrimethylammonium tetrabromide (2), and tetratributylammonium tetrabromide (3). Such nanoparticles were characterized by TEM, EDS, UV–vis, and IR. Their long-term dispersion stability varied significantly and depended on the nature of the resorcinarene headgroup, and in particular nanoparticles extracted by resorcinarene 1 were stable for several weeks. Nanoparticles passivated by resorcinarenes 1 and 2 were also stable in the presence of thiourea for several hours in both aqueous and organic medium. This is notable as thiourea is known to result in the instantaneous aggregation of citrate stabilized nanoparticles. Remarkably nanoparticles stabilized by resorcinarenes 1 and 2 could be precipitated and redispersed in chloroform without any visible aggregation. The critical parameters controlling the extraction of the nanoparticles into the organic phase have also been evaluated. The resorcinarene surfactant mediated facile phase transfer of gold nanoparticles described here can be readily applied for the stabilization of other citrate stabilized mono- and bimetallic nanoparticles, thus providing opportunities to disperse and stabilize relatively larger nanoparticles in organic solvents using ionic surfactants opening up new applications.