Ante versus post-functionalization to control surface structures with superhydrophobic and superoleophobic properties

Abstract

Here, we report the first use of Staudinger-Vilarrasa reaction with perfluorinated surface modification. Based on a 3,4-ethylenedioxythiophene (EDOT) monomer bearing azido groups, we develop ante and post deposition strategies in order to prepare functionalized surfaces. The Staudinger-Vilarrasa reaction allows to reduce the azido groups into amine functions and the reaction with carboxylic acids leads to amide bounds. Here, the surfaces are investigated for their morphologies and surface properties depending on the side chain length and the modification strategy. This work shows that various wettability properties from hydrophobic to superhydrophobic or oleophilic to superoleophobic can be obtained depending on both modification strategy and nature of the side chain.

Bifunctionalized Monomers for Surfaces with Controlled Hydrophobicity

“…For PEDOT‐Benz‐F 6 , the aggregates evolve to become spherical rough aggregates (Figure C) and cauliflower‐like structures are observed for PEDOT‐Benz‐F 8 (Figure D). This spherical morphology is consistent with the morphology observed for other perfluorinated PEDOTs reported in the literature . This change can be linked to the growing impact of the perfluorinated chain on the morphology.…”

“…However, owing to the properties of the triazole formed during the reaction and especially its basicity, which renders it not suitable for the electropolymerization process, this strategy is not suitable in our case . Also, based on the azido group reactivity, other click reactions such as the variation of the Staudinger reaction have been successfully used to prepare monomers suitable for functionalization . This efficient method allows us to graft various chains on monomers (alkyl, aryl, or perfluoroalkyl) …”

“…[30,31] Also, based on the azido group reactivity,o ther click reactions such as the variation of the Staudinger reactionh ave been successfully used to prepare monomers suitable for functionalization. [32] This efficient methoda llows us to graft variousc hains on monomers (alkyl, aryl, or perfluoroalkyl). [33] In this work, we focus on the possibility to use ao ne-pot sequentials ynthesis (Figure 1).…”

Azido Platform Surfaces for Post‐Functionalization with Aromatic Groups Using the Huisgen Reaction to Obtain High Water Adhesion

“…In the literature, different click‐chemistry reactions were investigated. For example, the Staudiger–Vilarassa reaction and the thiol–ene reaction were successfully reported as efficient tools for surface post‐functionalization . Among all the click chemistry reaction, the more popular and described reaction is the Huisgen reaction .…”

Surfaces Bearing Fluorinated Nucleoperfluorolipids for Potential Anti-Graffiti Surface Properties

“…The Staudinger-Vilarrasa reaction is known as a click-like reaction. This reaction has been successfully used to functionalize monomers before polymerization (ante approach) or to functionalize the surface after polymerization (post approach) [26].…”