Nucleoside surfaces as a platform for the control of surface hydrophobicity

Abstract

The control of the surface structures and surface energy of hydrophobic surfaces is extremely important for various potential applications. Here, we report for the first time the synthesis of 3,4-ethylenedioxythiophene (EDOT) derivatives with a nucleoside linker for surface post-functionalization using the Huisgen reaction. Various alkynes are used to graft alkyl, aryl or perfluoroalkyl chains. We show that it is possible to obtain both extremely high water contact angles (θ_water > 130°) and extremely high water adhesion (parahydrophobic properties). The highest θ_water values are obtained with fluorinated compounds but also surprisingly with phenanthrene. The extremely important results obtained with phenanthrene are explained by a change in the surface morphology after post-functionalization from cauliflower-like structures to fibrous structures. These key results are the first step in the study of the effect of nucleosides on the construction of hydrophobic surfaces.