Chemical and Electrochemical Synthesis of Highly Conductive and Processable PolyProDOP-alkyl Derivatives

Cho, Youn-Kyung; Pyo, Myoungho; Zong, Kyukwan

doi:10.5229/jkes.2010.13.1.057

Cited by 4 publications

(4 citation statements)

References 8 publications

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“…The fluorinated isocyanate was synthesized from a fluorinated acid chloride in the presence of trimethylsilyl azide . 2‐(2,3‐Dihydro‐[1,4]dioxino[2,3‐ c ]pyrrol‐6‐yl)ethanol (EDOP‐OH) was synthesized in ten steps from iminodiacetic acid using a procedure reported in the literature (Scheme ) …”

Section: Methodsmentioning

confidence: 99%

“…For instance, some derivatives of 3,4‐alkylenedioxypyrrole, such as, 3,4‐ethylenedioxypyrrole (EDOP), exhibit an exceptional polymerization capacity with one of the lowest oxidation potentials. Moreover, the resulting conducting polymers may also display unique optoelectronic properties . However, owing to the difficulty of synthesizing such derivatives (usually in more than eight steps), they have been only moderately studied in the literature so far.…”

Section: Introductionmentioning

confidence: 99%

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Bioinspired Rose‐Petal‐Like Substrates Generated by Electropolymerization on Micropatterned Gold Substrates

et al. 2016

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optimization of physical chemical methods to characterize nano-materials and nanostructures in order to study their interactions with cells and biomolecules and thereby assess their safety/bio-compatibility.S ubsequently,D r. Darmanin was made associate professor in the group of Prof. FrØdØric Guittard (NICE Lab, UniversitØ Côte d'Azur (UCA)). The focus of the group is to design novel su-perhydrophobic/superoleophobic surfaces by controlling the surface nanostructures (nanofibers, nanotubes, nanosheets) through electropolymerization. Moreover,t he adhesion of various liquids on these structured surfaces is studies. For such investigations, it is often necessary to combine two techniques to create micro-and nanoscale structures, in order to enhance the surface properties. Hence, collaboration was necessary to develop micro-patterned gold substrates by soft lithography (carried out at JRC) and to elec-tropolymerization on these substrates (carried out at NICE Lab). What are the main challengesi nthe broad area of your research? The main challenge in our field is the control of surface structures at both am icro-and nanoscale. Control of the surface is crucial to better understand the surface wetting properties from atheoretical point of view.V arious methods can be used to create micro-and nanostructures, lithographic techniques are probably the most flexible and can be applied to the design of well-defined, micropat-terned substrates. Electropolymerization is also au nique technique which induces the growth surface structures of various shapes (nanofibers, nanotubes, nanosheets, nanoparticles). What was the biggest surprise (on the way to the results presentedi nthis paper)? The biggest surprise was the huge influence of the micropattern-ing specifications (pillar diameter and pitch) and the electrochemi-cal parameters on the surface hydrophobicity and water adhesion. Moreover,i sw as possible to obtain the characteristics of extremely high apparent contact angles (up to 1608)a nd extremely high water adhesion, as observed in nature on rose petals. Such materials are extremely interesting for applications such as water harvesting and oil/water separation membranes. Invited for this month'sc over are the collaborating groups of Dr.T hierry Darmanin at UniversitØ Côte d'Azur,F rance and Dr.F ranÅois Rossi at JRC European Commission, Italy.T he cover picture shows an ovel strategy for preparing substrates having ar ose-petal effect (high water adhesion). The micropatterning specifications (pillar diameter and pitch) and the elec-tropolymerization parameters are key to obtaining both high water apparent contacta ngles and ah igh hysteresis. Read the full text of the article at

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Bioinspired Rose‐Petal‐Like Substrates Generated by Electropolymerization on Micropatterned Gold Substrates

et al. 2016

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“…The surface structures are highly dependent on electrochemical parameters and also on the monomer structure. It was shown that 3,4-ethylenedioxypyrrole (EDOP) and 3,4-propylenedioxypyrrole (ProDOP) derivatives have unique properties in term of polymerization capacity but also in terms of their optoelectronic − and wetting properties. Indeed, in comparison with classical pyrrole derivatives, the presence of two alkoxy groups in the 3 and 4 positions has several advantages.…”

Section: Introductionmentioning

confidence: 99%

3,4-Dialkoxypyrrole for the Formation of Bioinspired Rose Petal-like Substrates with High Water Adhesion

Mortier

Darmanin

2016

Langmuir

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Self-organization is commonly present in nature and can lead to the formation of surface structures with different wettabilities. Indeed, in nature superhydrophobic (low water adhesion) and parahydrophobic (high water adhesion) properties exist, such as in lotus leaves and red roses, respectively. The aim of this work is to prepare parahydrophobic properties by electrodeposition. For this, pyrrole derivatives with two alkoxy groups of various lengths (from 1 to 12) were synthesized in 8 steps by adapting a method developed by Merz et al. We show that the alkyl chain length has a huge influence on the polymer solubility and as a consequence on the surface morphology and hydrophobicity. Moreover, the alkyl chain length should be at least greater than eight carbons in order to obtain parahydrophobic properties. The properties are also controlled by the electrolyte nature. These materials can be used for many potential applications in water harvesting and transportation and separation membranes.

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“…Among the monomers usable for the electropolymerization, that of the 3,4-ethylenedioxypyrrole (EDOP) family offers exceptional polymerization capacity and lead to conducting polymers with unique optoelectronic properties. − However, due to the extreme difficulty to synthesize these monomers, usually obtained in about 10 steps, the study of these derivatives remains a challenge. − Previously, superoleophobic properties and superhydrophobic properties were obtained using fluorinated , and hydrocarbon chains, respectively. These exceptional properties were in part due to the presence of nanoporosity, which induces a high increase in the contact angles.…”

Section: Introductionmentioning

confidence: 99%

3,4-Ethylenedioxypyrrole (EDOP) Monomers with Aromatic Substituents for Parahydrophobic Surfaces by Electropolymerization

Mortier

Darmanin

2015

Macromolecules

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In nature, superhydrophobic (low adhesion) and parahydrophobic (high adhesion) properties exist in lotus leaves and red roses, for example. The control in the water adhesion is extremely important for applications in water harvesting, for example. Here, we report the obtaining of parahydrophobic properties through the electropolymerization of 3,4-ethylenedioxypyrrole (EDOP) derivatives. We report for the first time an electrochemical study of EDOP derivatives bearing aromatic cycles (phenyl, naphthalene, biphenyl, and pyrene). Eight novel EDOP monomers are studied with and without the presence of an ethyl acetate spacer in order to give more mobility to the aromatic substituents. Surprinsgly, higher steric hindrance are observed during electropolymerization with spacer. However, the polymers are more insoluble with spacer, which is an important point for electropolymerization. The highest parahydrophobic properties are obtained with biphenyl groups and with the spacer, which are due to the presence of both micro-and nanostructures.

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Chemical and Electrochemical Synthesis of Highly Conductive and Processable PolyProDOP-alkyl Derivatives

Cited by 4 publications

References 8 publications

Bioinspired Rose‐Petal‐Like Substrates Generated by Electropolymerization on Micropatterned Gold Substrates

Bioinspired Rose‐Petal‐Like Substrates Generated by Electropolymerization on Micropatterned Gold Substrates

3,4-Dialkoxypyrrole for the Formation of Bioinspired Rose Petal-like Substrates with High Water Adhesion

3,4-Ethylenedioxypyrrole (EDOP) Monomers with Aromatic Substituents for Parahydrophobic Surfaces by Electropolymerization

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