Azidomethyl-EDOT as a Platform for Tunable Surfaces with Nanostructures and Superhydrophobic Properties

Godeau, Guilhem; N'Na, Jessica; Darmanin, Thierry

doi:10.1021/acs.jpcb.5b03462

Cited by 25 publications

(27 citation statements)

References 45 publications

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“…[ 38,39 ] 0.5 g of (4-hydroxymethyl)-EDOT (2.9 mmol) was dissolved in dry THF (10 mL). 83.5 mg of sodium hydride (3.5 mmol, 1.2 eq) was added at 0 °C.…”

Section: Synthesismentioning

confidence: 99%

Postfunctionalization of Azido or Alkyne Poly(3,4‐ethylenedioxythiophene) Surfaces: Superhydrophobic and Parahydrophobic Surfaces

Godeau

N'Na

Boutet

et al. 2015

Macro Chemistry & Physics

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Postfunctionalization is a key tool for the elaboration of hydrophobic surfaces. For that purpose, the elaboration of surfaces suitable for the Huisgen reaction allows for functionalization with various hydrophobic side chains. Here the synthesis of azido or alkyne monomers is reported to prepare platform surfaces suitable for click chemistry. The surface hydrophobicity and morphology are investigated. Superhydrophobic and parahydrophobic properties are obtained depending on the starting monomer and the molecule used for the postfunctionalization. species are characterized by high θ w but also extremely high H w as observed on rose petals and gecko foot. [11][12][13] These surface properties are called parahydrophobic. [ 14 ] Usually, superhydrophobic properties are obtained by combining high surface roughness (often both of the micro and nanoscale) and low surface energy materials. [ 15,16 ] However, the water adhesion can be controlled by playing with the geometry of the surface structures or by lowering the surface energy. [17][18][19][20] In order to prepare these types of surfaces different approaches can be imagined. [3][4][5][6] It is possible to make physical or optical structuration on hard surfaces, which can be seen as a top down approach. Another option is the possibility of preparing surface starting from low molecular weight materials, which can be described as bottom-up approach. The bottom-up approach can be divided in two different strategies: the ante -and the poststrategies. Modifi cations can be added on the small molecules before the surface elaboration ( ante -strategy) or the modifi cations can be linked on the formed surfaces (poststrategy). Conducting polymers are good candidates for surfaces made with the bottom up approach. The modifi cation can be made on the monomer ( ante ) [ 21 ]

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“…[ 38,39 ] 0.5 g of (4-hydroxymethyl)-EDOT (2.9 mmol) was dissolved in dry THF (10 mL). 83.5 mg of sodium hydride (3.5 mmol, 1.2 eq) was added at 0 °C.…”

Section: Synthesismentioning

confidence: 99%

Postfunctionalization of Azido or Alkyne Poly(3,4‐ethylenedioxythiophene) Surfaces: Superhydrophobic and Parahydrophobic Surfaces

Godeau

N'Na

Boutet

et al. 2015

Macro Chemistry & Physics

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“…In the literature, the functionalization by azido groups is widely employed to perform modification by the Huisgen reaction (click chemistry) [17,18,27]. In this work, we reported for the first time that the Staudinger-Vilarrasa reaction can also be used with azido groups for surface modification by formation of amide linkers.…”

Section: Resultsmentioning

confidence: 97%

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

Godeau

Darmanin

2015

Journal of Colloid and Interface Science

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“…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 .…”

Section: Introductionmentioning

confidence: 99%

Bifunctionalized Monomers for Surfaces with Controlled Hydrophobicity

et al. 2017

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The control of surface wettability is a key parameter for many application fields (materials, biomedical engineering, etc.). In this work, a new and efficient strategy to synthesize monomers suitable for hydrophobic surface elaboration is reported. This original approach allows the preparation of monomers and, as a consequence, surfaces bearing two different substituents by using the Staudinger reductive amination and amidification. Rough conducting polymer films were prepared by electropolymerization. The original surfaces reported here are highly structured surfaces with tunable hydrophobic features. Depending on the grafted chains, the surfaces are hydrophilic (PEDOT‐Benz‐Ph, θ=80 °; PEDOT=poly(3,4‐ethylenedioxythiophene)), hydrophobic (PEDOT‐Benz‐C12, θ=132 °), or even superhydrophobic (PEDOT‐Benz‐F8, θ=152 ° (α=5.0 °, H=0.3 °).

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Azidomethyl-EDOT as a Platform for Tunable Surfaces with Nanostructures and Superhydrophobic Properties

Cited by 25 publications

References 45 publications

Postfunctionalization of Azido or Alkyne Poly(3,4‐ethylenedioxythiophene) Surfaces: Superhydrophobic and Parahydrophobic Surfaces

Postfunctionalization of Azido or Alkyne Poly(3,4‐ethylenedioxythiophene) Surfaces: Superhydrophobic and Parahydrophobic Surfaces

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

Bifunctionalized Monomers for Surfaces with Controlled Hydrophobicity

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