Design, Synthesis, and Characterization of Novel Thiol-Derivatized Ibuprofen Monolayer Protected Gold Clusters

• Main Authors: Kuan-Han Lee, Yu-Sheng Lin, Po-Jui Huang
• Format: Article
• Language: English
• Published: Hindawi Limited 2013-01-01
• Series: Journal of Nanomaterials
• Online Access: http://dx.doi.org/10.1155/2013/931815

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 amide 2, and N-hydroxyphenyl amide 6, which were then tosylated with p-toluenesulfonyl chloride at hydroxyl group to give 3 and 7. Reactions of 3 and 7 with NaSH afforded the mercapto derivatives 4 and 8. Conducting Brust’s reaction with a 3 : 1 mole ratio of thiolate ibuprofen/AuCl4- yielded polydisperse thiol-derivatized ibuprofen-MPCs 5 and 9. All compounds have been identified by NMR, MS, UV, and IR spectroscopies. Compounds 4 and 8 and the MPCs 5 and 9 have been investigated by using the method of 1H NMR spectroscopy. The broadening of the signals from 0.8 to 2.0 ppm in 1H NMR spectrum of MPCs 5 and 9 confirmed the success of the conjugation of thiol-containing derivatives with nanogold cluster.