Soft-template electropolymerization of 3,4-(2,3-naphtylenedioxy)thiophene-2-acetic acid esters favoring dimers: Controlling the surface nanostructure by side ester groups

Fradin, Caroline; Guittard, Frédéric; Perepichka, Igor F.; Darmanin, Thierry

doi:10.1016/j.electacta.2022.140684

Cited by 5 publications

(4 citation statements)

References 83 publications

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“…It is well established in conjugated polymers that π ‐stacking interactions can induce this effect in the direction perpendicular to the molecule, as already reported with 3,4‐naphthalenedioxythiophene (NaphDOT) [27] . Because the preferential growth needs time, the polymerization speed should not be too fast also, as already reported by designing monomers leading to only dimers during electropolymerization or by reducing the electropolymerization temperature [31,32] . Wang et al.…”

Section: Introductionmentioning

confidence: 76%

“…[27] Because the preferential growth needs time, the polymerization speed should not be too fast also, as already reported by designing monomers leading to only dimers during electropolymerization or by reducing the electropolymerization temperature. [31,32] Wang et al reported 1,3,5-tri(thiophen-2-yl)benzene (Ph-2-Th) as an excellent monomer by soft-template electropolymerization in similar conditions. [33] Here (Scheme 1), we study also a close monomer differing by the position of the thiophene groups (Ph-3-Th) as well as various original carbazole-based monomers (Ph-p-Cb, Ph-m-Cb, Ph-o-Cb, Ph-p-PhÀ Cb, Ph-2-CbÀ Ph, Ph-3-CbÀ Ph, Ph-3-CbÀ Na).…”

Section: Introductionmentioning

confidence: 99%

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Bioinspired Nanotubes by Soft‐template Electropolymerization from Fully Conjugated Monomers

Dione,

Dramé,

Diouf

et al. 2023

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Bioinspired by the strong water‐adhesive forces of gecko foot or rose petals, here, nanotubular structures are prepared by soft‐template electropolymerization. Water is mixed to a solvent of low water‐solubility to form a micellar solution in the presence of tetrabutylammonium perchlorate as the electrolyte and surfactant. As the monomer, a benzene is trifunctionalized with various thiophene and carbazole moieties. The monomers are fully conjugated to favor the deposition compared to polymerization, as confirmed by cyclic voltammetry experiments. The surface nanostructures (nanotubes, nano‐ribbons, coral‐like structures) are highly dependent on the monomer and the water content but less on the deposition method. The maximum water contact angle is 158.1° accompanied with strong water adhesive force. These surfaces are highly interesting for applications in water‐harvesting systems or in sensing platforms.

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Section: Introductionmentioning

confidence: 76%

Section: Introductionmentioning

confidence: 99%

Bioinspired Nanotubes by Soft‐template Electropolymerization from Fully Conjugated Monomers

Dione,

Dramé,

Diouf

et al. 2023

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“…Previously, we demonstrated using NaphDOT that even if one substituent is positioned in polymerization position (2-position) leading to dimers, the resulting polymer can be sufficiently insoluble to form deposit and use in soft-template electropolymerization [31]. This is mainly due to the strong π-stacking interactions.…”

Section: Introductionmentioning

confidence: 99%

Bioinspired Nanotubular Structures by Soft-Template Electropolymerization: 3,4-(2,3-naphtylenedioxy)Thiophene Monomers Quenched to Form Dimers

Sow,

Dramé

et al. 2024

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Preparing well-ordered nanotubes on materials surface is a great of interest in many applications. Bio-inspired and theoretical approaches show that porous structures such as nanotubes are key parameters for both surface hydrophobicity and water adhesion. Here, a very easy soft-template electropolymerization approach is used to form nanotubular structures, followed by a bioinspired strategy to control the wetting properties. Fully conjugated monomers based on 3,4-(2,3- naphtylenedioxy)thiophene (NaphDOT) core grafted with many rigid aromatic groups such as phenyl, naphthalene, pyrene, pyrrole, were synthesized. Then, electropolymerization is carried out with these monomers, followed by surface and morphologies characterization of corresponding polymers. We show that even if just dimers are formed by electropolymerization, the resulting polymer can be sufficiently insoluble to form structured films. 3,4-(2,3-naphtylenedioxy)thiophene (NaphDOT) is chosen as a judicious example, due to strong π-stacking interactions, and also their capacity to form nanotubular structures by soft template-electropolymerization in the presence of water (H2O). Here, different substituents, polymerizable or not, are grafted on the 2-position of thiophene. Films are formed with all the studied substituents. Nanotubular structures are especially observed with the following substituents: hydroxyl, pyrene and pyrrole, but in the presence of H2O. We study also their influence on the surface hydrophobicity.

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“…Several synthetic methodologies including electrochemical, 1–3 chemical oxidative 4–6 and transition metal-catalyzed cross-coupling reactions 7–10 have been investigated for the synthesis of π-conjugated organic and polymeric materials. Direct C–H arylation reaction has been proved to be a particularly efficient methodology for the formation of carbon–carbon bonds without the use of organometallic nucleophiles.…”

Section: Introductionmentioning

confidence: 99%

Polymers based on thieno[3,4-c]pyrrole-4,6-dione and pyromellitic diimide by CH–CH arylation reaction for high-performance thin-film transistors

et al. 2022

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Soft-template electropolymerization of 3,4-(2,3-naphtylenedioxy)thiophene-2-acetic acid esters favoring dimers: Controlling the surface nanostructure by side ester groups

Cited by 5 publications

References 83 publications

Bioinspired Nanotubes by Soft‐template Electropolymerization from Fully Conjugated Monomers

Bioinspired Nanotubes by Soft‐template Electropolymerization from Fully Conjugated Monomers

Bioinspired Nanotubular Structures by Soft-Template Electropolymerization: 3,4-(2,3-naphtylenedioxy)Thiophene Monomers Quenched to Form Dimers

Polymers based on thieno[3,4-c]pyrrole-4,6-dione and pyromellitic diimide by CH–CH arylation reaction for high-performance thin-film transistors

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