Epoxidation of the surface of polydicyclopentadiene for the self-assembly of organic monolayers

Abstract

Polydicyclopentadiene was reacted with m-chloroperoxybenzoic acid to yield a surface that was terminated with epoxides. The X-ray photoelectron spectrum (XPS) of the sample demonstrated that the top ten nm of the surface had been oxidized. The grazing angle attenuated total reflection-infrared spectrum of this surface was unchanged from that of native PDCPD which demonstrated that the oxidation was only on the surface and that the bulk PDCPD was unchanged. The PDCPD–epoxide surface was then reacted with two different amines that possessed F or Cl atoms to study the ring opening reaction between surface epoxides and amines. This reaction was rapid and completed within an hour. The method of Tougaard was applied to the F and Cl peaks in the XPS to investigate their locations and whether the amines were uniformly distributed in the top ten nm or were localized at the surface. This analysis clearly described the amines as being present only on the surface. The PDCPD–epoxide surface was also reacted with poly(ethylene imine) to generate a surface that exposed numerous amines. The amines bonded to Cu such that this metal did not flux through PCPCD while the flux of 4-nitrobenzaldehyde was unaffected.