Remarkable high-yielding chemical modification of gold nanoparticles using uncatalyzed click-type 1,3-dipolar cycloaddition chemistry and hyperbaric conditions

Azide-terminated alkyl thiolate mono layer-protected gold nanoparticles (1-C12MPN) with a core size of 1.8 +/- 0.2 nm were prepared. 1-C12MPN was modified in high yields via an uncatalyzed 1,3-dipolar cycloaddition (click-type reaction) with a variety of terminal acyl-alkynes under hyperbaric conditions at 11 000 atm. The resulting 1,2,3-triazole modified MPNs (2-C12MPN) were characterized using H-1 NMR spectroscopy and were verified by comparison of the spectra to those obtained for the products of the model reactions of 1-azidododecane with the same alkynes. TEM analysis showed that the high-pressure conditions did not affect the size of the gold core, suggesting that the only effect is to facilitate the chemical reaction on the particles.