Design, Synthesis, and Characterization of Novel Thiol-Derivatized Ibuprofen Monolayer Protected Gold Clusters
A series of new thiol-derivatized ibuprofen monolayer protected gold clusters have been prepared by amidation of ibuprofen with alkyl alcohol or aminophenol affording the carboxamides, N-hydroxyalkyl amide2, and N-hydroxyphenyl amide6, which were then tosylated withp-toluenesulfonyl chloride at hydroxyl group to give3and7. Reactions of3and7with NaSH afforded the mercapto derivatives4and8. Conducting Brust’s reaction with a 3 : 1 mole ratio of thiolate ibuprofen/AuCl4-yielded polydisperse thiol-derivatized ibuprofen-MPCs5and9. All compounds have been identified by NMR, MS, UV, and IR spectroscopies. Compounds4and8and the MPCs5and9have been investigated by using the method of1H NMR spectroscopy. The broadening of the signals from 0.8 to 2.0 ppm in1H NMR spectrum of MPCs5and9confirmed the success of the conjugation of thiol-containing derivatives with nanogold cluster.