Staudinger-Vilarassa reaction versus Huisgen reaction for the control of surface hydrophobicity and water adhesion

Abstract

Surface modifications are keys for a great number of applications. In order to perfectly control the surface properties, it is important to control the modification pathways. Two general pathways can be described in order to introduce modification on surfaces: the post-strategies and the ante-strategies. In this work, we focus on the comparison between the Huisgen and the Staudinger-Vilarrasa reaction for both post-surface and ante-surface modifications. Here, we focused on the possibility to use both two reactions to obtain superhydrophobic and oleophobic properties. This work includes monomer synthesis, surface modifications with alkyl, aryl or perfluoroalkyl chain.

Poly(3,4-ethylenedioxythiophene) (PEDOT) Derivatives: Innovative Conductive Polymers for Bioelectronics

“… Most representative functional EDOT monomers synthesized from azidomethyl-EDOT using click chemistry: ( a ) aliphatic, ferrocene phtalamide [ 50 , 52 ], ( b ) fluorinated ester, substituted xantene [ 51 ], ( c ) sugar, bipyridine, naphtalenediimide, substituted fullerene [ 63 ], ( d ) plain aliphatic chains [ 49 , 64 ], ( e ) plain aromatic groups [ 65 ], ( f ) fluorinated ester [ 64 ], ( g ) fluorinated aromatic, primary alcohol [ 53 ], and ( h ) sulfonate salt, have all been connected to the EDOT scaffold via a triazole spacer [ 66 ]. …”

Bio-Inspired Polymeric Structures with Special Wettability and Their Applications: An Overview

“…Over the last few decades, a variety of techniques have been reported to develop superhydrophobic surfaces, including electrospinning, spray coating, mold transfer, UV treatment, laser structuring, polymerization, layer–layer assembly, chemical/electro vapor deposition, nano imprinting, dip-coating, and click-chemistry (Thiol-Yne click-chemistry, Huisgen reactions, Staudinger–Vilarrasa reactions) [ 149 , 150 , 151 , 152 , 153 , 154 , 155 , 156 , 157 , 158 , 159 , 160 , 161 , 162 , 163 , 164 , 165 , 166 , 167 , 168 , 169 , 170 , 171 , 172 , 173 , 174 , 175 ]. Zhang et al [ 165 ] fabricated superhydrophobic and self-cleaning surfaces using laminating exfoliation ( Figure 10 ).…”

Bifunctionalized Monomers for Surfaces with Controlled Hydrophobicity

“…This reaction has been reported for successful post‐functionalization of conductive polymer surfaces . 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 .…”

“…[28,29] However,o wing to the properties of the triazole formed duringt he reaction and especially its basicity,w hich renders it not suitable for the electropolymerization process, this strategy is not suitable in our case. [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).…”