A platform on metal oxide surfaces suitable for copper-catalyzed azide-alkyne cycloaddition (CuAAC), or click chemistry, provides a route to many future reactions. To this end, diethyl 2-bromoethyl phosphonate is used in a series of reactions to yield a phosphonic acid and an azide on opposing ends of the molecule: the azide allows for the click reaction, while the phosphonic acid allows for the molecule to bond to a metal oxide surface. Deprotection of the phosphonate yields the phosphonic acid, which is then attached to a copper oxide surface by a Tethering By Aggregation and Growth (TBAG) deposition method. The azide is attached to the surface-bound phosphonate by performing a backside attack on the terminal bromine using sodium azide. A CuAAC click reaction is used to react the azide with a model terminal alkyne to form the 1,4-substituted 1,2,3-triazole. Surface modification is confirmed via specular reflectance infrared spectroscopy.

Modifying copper surfaces with azide-terminated phosphonic acids: A platform for surface functionalization via click chemistry

245th National Meeting (2013)

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