By attaching an azide-terminated compound to a metal oxide surface through a phosphonic acid head-group, a surface bound molecule with the ability to participate in click chemistry is generated. Through a copper-catalyzed azide-alkyne cycloaddition (CuAAC) click reaction, a transition metal catalyst can be attached to the metal oxide, provided one of the ligands has a terminal alkyne. Two compounds, diethyl 2-bromoethylphosphonate and 11-hydroxyundecylphosphonic acid, were used to modify a metal oxide surface and, subsequently, perform CuAAC with the azide-terminus to form a triazole.The ethoxy groups of diethyl 2-bromoethylphosphonate were removed via a deprotection reaction, converting the phosphonate moiety to a phosphonic acid (99% yield). The Tethering By Aggregation and Growth (TBAG) deposition method was used to covalently bind this compound to a copper oxide surface through the phosphonic acid head-group before being used in an in-situ CuAAC reaction, which both attaches an azide and forms a triazole. 11-Hydroxyundecylphosphonic acid was attached to a copper surface through the same deposition method. The hydroxyl group was then converted into either a bromo or mesyl intermediate and successively reacted in an in-situ CuAAC reaction with either model compounds or a ruthenium complex containing a ligand with a terminal alkyne. Surface reflectance infrared (IR) spectroscopy was used to verify surface modifications.

Metal oxide surface modification with a ruthenium catalyst via CuAAC

248th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.