Electrochemical synthesis of PEDOT derivatives bearing imidazolium‐ionic liquid moieties

Döbbelin, Markus; Pozo‐Gonzalo, Cristina; Marcilla, Rebeca; Blanco, Raúl; Segura, José L.; Pomposo, José A.; Mecerreyes, David

doi:10.1002/pola.23384

Cited by 47 publications

(35 citation statements)

References 66 publications

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“…Annotation: For both polymers PEDOT-ImBF 4 Cl and PEDOT-ImTFSI broad bands were observed in the 1 H NMR spectra, hindering a clear detection of each proton. A clear separation of the proton signals can be seen in the 1 H NMR spectra of the corresponding monomers [24].…”

Section: Methodsmentioning

confidence: 88%

“…Poly [1,4]dioxin-2-yl)methyl)-1-methyl-1H-imidazol-3-ium tetrafluoroborate (EDOT-ImBF 4 ) was synthesized as previously described [24]. Monomer EDOT-ImBF 4 (0.1 g, 0.3 mmol) and 3.3 equivalents of anhydrous iron(III) chloride (>98%) were added to chloroform (15 mL).…”

Section: Methodsmentioning

confidence: 99%

“…PEDOT-ImBF 4 Cl was first synthesized by oxidative coupling of the 3-((2,2-dihydrothieno [3,4-b] [1,4]dioxin-2-yl)methyl)-1-methyl-1H-imidazol-3-ium tetrafluoroborate (EDOT-ImBF 4 ) monomer [24] in the presence of iron(III) chloride. By this method, a dark blue, solid polymer precipitate was obtained in chloroform.…”

Section: Chemical Synthesis Of Multiresponsive Pedot-im Polymersmentioning

confidence: 99%

“…Using a similar approach, we reported on the electropolymerization of new PEDOT derivatives with pendant imidazolium ionic-liquid moieties (PEDOT-Im). [24] In this article, new PEDOT-Im materials are presented with an emphasis on their unique multiresponsive properties and their application in the design of smart surfaces. These new materials are investigated with respect to their responsiveness to pH, oxidizing agents, temperature, and anions, in solution and as solid thin films.…”

Section: Introductionmentioning

confidence: 99%

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Multiresponsive PEDOT–Ionic Liquid Materials for the Design of Surfaces with Switchable Wettability

Döbbelin

Tena‐Zaera

Marcilla

et al. 2009

Adv Funct Materials

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Among the different types of stimuli‐responsive polymers, conjugated polymers reveal unique multiresponsive behavior. In this work, the synthesis and characterization of new functional poly(3,4‐ethylenedioxythiophenes) (PEDOT) bearing imidazolium ionic‐liquid moieties (PEDOT‐Im) is reported. PEDOT‐Im polymers show multiresponsive properties to a variety of stimuli, such as temperature, pH, oxidative doping, and presence of anions. These stimuli provoke different changes in PEDOT‐Im, such as changes in color, oxidation state, and, wetting behavior. In all cases, a reversible effect is observed, and the polymers reveal responsive properties in solution as well as in the form of thin films. Whereas sensitiveness to pH and oxidative doping are known phenomena for other PEDOT derivatives, responsiveness to temperature and to anions is a unique property of PEDOT‐Im. The anion exchange is further investigated by means of the Quartz Crystal Microbalance with dissipation. Anion exchanges induce fast, adjustable, and reversible contact angle changes between 24° and 107°. As a potential application, surfaces with switchable wettability triggered by anion solutions are prepared by spin‐coating PEDOT‐Im films onto different substrates.

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Section: Methodsmentioning

confidence: 88%

Section: Methodsmentioning

confidence: 99%

Section: Chemical Synthesis Of Multiresponsive Pedot-im Polymersmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Multiresponsive PEDOT–Ionic Liquid Materials for the Design of Surfaces with Switchable Wettability

Döbbelin

Tena‐Zaera

Marcilla

et al. 2009

Adv Funct Materials

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“…For example, multiresponsive surfaces were obtained by grafting an imidazolium substituent on PEDOT polymers [101,102]. Smooth polymer films were prepared by spin-coating and observed sensitivity to ion exchange, oxidative doping, temperature, and pH.…”

Section: Dual Sensitivitymentioning

confidence: 99%

Switchable and Reversible Superhydrophobic Surfaces: Part Two

Taleb¹,

Darmanin²,

Guittard³

2018

Interdisciplinary Expansions in Engineering and Design With the Power of Biomimicry

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In this book chapter, most of the methods used in the literature to prepare switchable and reversible superhydrophobic surfaces are described. Inspired by Nature, it is possible to induce the Cassie-Baxter-Wenzel transition using different external stimuli such as light, temperature, pH, ion exchange, voltage, magnetic field, mechanic stress, plasma, ultrasonication, solvent, gas or guest. Such properties are extremely important for various applications but especially for controllable oil/water separation membranes, oil-absorbing materials, and water harvesting systems.Keywords: superhydrophobic, reversible, switchable, bioinspiration, biomimetism Reversible superhydrophobic surfaces: Part twoThis section provides continuation of the description of the stimuli used in the literature to induce reversible changes in surface wettability. Ion exchangeSince 2004, the researchers have shown that the presence of charged species such as quaternary ammonium groups are sensitive to ion exchange and lead to different surface wettabilities. In 2004, Choi et al. prepared self-assembled monolayers (SAM) with imidazolium groups on smooth Au and Si/SiO 2 substrates [1][2][3]. They studied the effect of a series of anions as shown in Figure 1 and In order to elaborate reversible superhydrophobic properties by ion exchange, gold micro and nanostructured substrates were performed by electroless etching process by immersing silicon substrates in aqueous solution of HAuCl 4 and HF (Figure 2). The surface was then modified by SAM using a thiol terminated by a quaternary ammonium. Then, the surface wettability could be reversely changed from superhydrophilic to superhydrophobic after [20]. Here, the presence of TSPM (sol-gel precursor) was used not only to form a polymer network via intramolecular interactions but also to anchor substrates (Figure 3). The membranes could reversely change from superhydrophobic/highly oleophobic to superhydrophilic/superoleophobic after exchanging Cl − ions by heptadecafluorooctanesulfonic acid (C 8 F 17 SO 3 − or HPS − ) ions. Moreover, the membranes were also highly efficient filter medium for removing multiple contaminants such as SO 2 form waster gas streams. A nother strategy was to deposit polyelectrolyte multilayers poly(diallyldimethylammonium chloride (PDDA) and poly(sodium 4-styrenesulfonate) (PSS) on gold micro and nanostructured substrates [21]. The authors studied the influence of the exchanged ions and the highest properties were obtained by exchanging Cl − (θ w < 5°) ions by PFO − (θ w = 164°). The authors also deposited polyelectrolyte multilayers on micro and nanostructured aluminum substrates obtained by etching in HCl and immersion in boiling water [22,23]. Using PFO − ions, the substrates were superhydrophobic and superoleophobic. When the substrates were immersed in seawater, the PFO − ions were exchanged by hydrophilic Cl − or SO 4 2− making the substrates underwater superoleophobic. Magnetic fieldEnvironment protection against oil leakage during oil tankers sinking is ...

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Polymer Brushes

Yoshizawa‐Fujita

Ohno

2011

Electrochemical Aspects of Ionic Liquids

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Electrochemical synthesis of PEDOT derivatives bearing imidazolium‐ionic liquid moieties

Cited by 47 publications

References 66 publications

Multiresponsive PEDOT–Ionic Liquid Materials for the Design of Surfaces with Switchable Wettability

Multiresponsive PEDOT–Ionic Liquid Materials for the Design of Surfaces with Switchable Wettability

Switchable and Reversible Superhydrophobic Surfaces: Part Two

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