Staudinger Vilarassa reaction: A powerful tool for surface modification and superhydrophobic properties

Godeau, Guilhem; Darmanin, Thierry

doi:10.1016/j.jcis.2015.06.032

Cited by 20 publications

(15 citation statements)

References 30 publications

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“…The 3,4‐ethylenedioxythiophene part was selected for their exceptional electrochemical properties. This monomer is prepared in three steps starting from the 3,4‐dimethoxythiophene ( Scheme ), as already reported in literature …”

Section: Resultsmentioning

confidence: 99%

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Combining Staudinger Reductive Amination and Amidification for the Control of Surface Hydrophobicity and Water Adhesion by Introducing Heterobifunctional Groups: Post‐ and Ante‐Approach

Kout

Trad

Kateb

et al. 2017

Macro Chemistry & Physics

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Here, the combination of both the Staudinger reductive amination and amidification to prepare highly hydrophobic surfaces is reported for the first time. This approach has been studied for surface ante and post‐deposition modification. In the ante‐deposition approach, the combination of both the reactions allows to develop a one‐pot new monomer bearing two different side chains (heterobifunctional surface). The developed monomer has been successfully polymerized and leads to hydrophobic surface (θ > 110°). Similar modifications performed as post‐treatment lead to highly hydrophobic feature (θ > 120°). The difference between the ante and post‐deposition modification is investigated for their roughness and morphologies. The results of this work allow explaining this difference on surface feature and show quality and drawback of both ante and post‐deposition strategies.

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Section: Resultsmentioning

confidence: 99%

“…This monomer is prepared in three steps starting from the 3,4-dimethoxythiophene (Scheme 1), as already reported in literature. [41] EDOT-N 3 monomer is suitable for both reaction (antestrategy) and polymerization (post-strategy). In the ante-strategy, a new monomer has been prepared (EDOT-amide-Ph-C 10 ).…”

Section: Synthesismentioning

confidence: 99%

Combining Staudinger Reductive Amination and Amidification for the Control of Surface Hydrophobicity and Water Adhesion by Introducing Heterobifunctional Groups: Post‐ and Ante‐Approach

Kout

Trad

Kateb

et al. 2017

Macro Chemistry & Physics

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“…The selected electropolymerizable part is a 3,4-ethylenedioxythiophene (EDOT) derivative with a butyl spacer. 35 Here, the monomer is used with a spacer in order to decrease the steric hindrance between the monomer and the nucleoside. This decrease is an important element for both polymerization and nucleoside self-assembly.…”

Section: Synthesismentioning

confidence: 99%

Nucleoside surfaces as a platform for the control of surface hydrophobicity

Godeau

Guittard

2016

RSC Adv.

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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 (q water > 130 ) and extremely high water adhesion (parahydrophobic properties). The highest q 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.

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“…Among the post-functionalization strategies, those involving click chemistry appear to be very interesting [23]. Different reactions such as thiol-Michael addition [24] or Staudinger Vilarassa [25,26] were reported but the more studied is the Huisgen reaction catalyzed with copper [27,28]. The Huisgen reaction allows for ligation between azide and alkyne by forming a 1,2,3-triazole.…”

Section: Introductionmentioning

confidence: 99%

Nanoparticle covered surfaces: An efficient way to enhance superhydrophobic properties

2016

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Staudinger Vilarassa reaction: A powerful tool for surface modification and superhydrophobic properties

Cited by 20 publications

References 30 publications

Combining Staudinger Reductive Amination and Amidification for the Control of Surface Hydrophobicity and Water Adhesion by Introducing Heterobifunctional Groups: Post‐ and Ante‐Approach

Combining Staudinger Reductive Amination and Amidification for the Control of Surface Hydrophobicity and Water Adhesion by Introducing Heterobifunctional Groups: Post‐ and Ante‐Approach

Nucleoside surfaces as a platform for the control of surface hydrophobicity

Nanoparticle covered surfaces: An efficient way to enhance superhydrophobic properties

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