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Poster De Conférence Année : 2023

Pyrrole-tailed imidazolium surface-active monomers: aggregation properties in aqueous solution and polymerization behavior

Résumé

Since 2004, aggregation of Ionic Liquids (ILs) in water has been widely studied both experimentally and using computational studies. In particular, imidazolium cations with long alkyl chains and associated with halogenated counterions have been demonstrated to self-assemble to form micelles in aqueous solutions. Surfactants that contain a polymerizable functional groups are called surfmers. Poly(ionic liquid)s (PILs), otherwise known as polymerized ionic liquids, are a subclass of polyelectrolytes that comprises an ionic liquid (IL) species in each monomer repeating unit, connected through a polymeric backbone. PILs that possess an intrinsically conducting polymers (ICP) backbone like polypyrrole have been synthesized with the objective to combine ionic and electronic conducting properties in the same polymers. Some studies have taken benefit from the surfactant properties of imidazolium and pyridinium-based molecules bearing a terminal pyrrole group to elaborate ordered mesoporous silica structure with aligned polypyrrole nanowires in channels. Imidazolium-tailed pyrrole surfactants were more recently used as fluidic light sensing materials for preparing flexible optoelectronic sensors and were also electrochemically polymerized to obtain polypyrrole films with wrinkle structure. Surprisingly, the surfactant behavior of these pyrrole-functionalized imidazolium PyCnMImBr molecules has never been studied in detail. Besides that, in recent years, special attention has been paid to the development of conjugated polymer nanoparticles (CPNs). Indeed, CPNs possess several advantages for biological imaging and sensing applications like their high brightness, large extinction coefficients, superior photostability, low cytotoxicity, facile chemical synthesis and tunable spectral properties. Here, the objective of this study was double: we firstly investigated the surfactant properties of the ILS PyCnMImBr with different alkyl chain lengths (n = 8, 10,12) by means of tensiometry and conductimetry. We demonstrated that Critical Aggregation Concentrations (CACs) of these PyCnMImBr were lower than their non-functionalized analogues due to (i) an increased hydrophobicity resulting from the extension of the alkyl chain length upon incorporation of pyrrole (ii) the formation of attractive pp interactions among pyrrole. 1H nuclear magnetic resonance measurements were used to shed light on the structure of the aggregates formed. We thereafter develop an easy and simple to implement method to prepare water-stable polypyrrole nanoparticles. For this, micelles obtained with PyC12MImBr were further used as nano-reactor to prepare water-stable polypyrrole. Infrared (IR) and Dynamic Light Scattering (DLS) measurements, confirmed the formation of polypyrrole particles of about 4 nm that were water-stable thanks to the presence of cationic imidazolium functions on their surface. These nanoparticles might find applications as interlayers of organic light emitting diodes (OLEDs), antistatic coatings and as inkjet-printed chemical sensors.

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Chimie
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Dates et versions

hal-04517827 , version 1 (22-03-2024)

Identifiants

  • HAL Id : hal-04517827 , version 1

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Lydie Viau, Stéphanie Beffy, Emmanuel Contal, Cédric Buron. Pyrrole-tailed imidazolium surface-active monomers: aggregation properties in aqueous solution and polymerization behavior. COIL-9 Congress on Ionic Liquids, Apr 2023, Lyon, France. . ⟨hal-04517827⟩
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