Carbonate-Terminated Self-Assembled Monolayers for Mimicking Nanoscale Polycarbonate Surfaces

Abstract

Two carbonate-terminated alkanethiol molecules having different positional isomers of a six-membered cyclic carbonate group, 3-COC12SH and 2-COC12SH, were synthesized and used to generate self-assembled monolayers (SAMs) on gold to serve as mimics of the surfaces of commercially available poly(propylene carbonate) (PPC) and poly(ethylene carbonate) (PEC). The adsorbate molecules were characterized using 1H and 13C nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry. The corresponding SAMs on gold were characterized by ellipsometry, contact angle goniometry, polarization-modulation infrared reflection-adsorption spectroscopy, and X-ray photoelectron spectroscopy. The contact angle data showed that the wettabilities of both SAMs were largely similar to each other and to the PEC samples for a wide range of contacting probe liquids (with water correlating particularly well with PEC and both SAMs). As a whole, the wettability data suggest that the carbonate-terminated SAMs can serve as mimics of nanoscale polycarbonate surfaces and can be used to investigate the interfacial properties of polycarbonates without interference from the surface reconstruction.