Combination of phosphonium and ammonium pendant groups in cationic conjugated polyelectrolytes based on regioregular poly(3-hexylthiophene) polymer chains

[Display omitted] •Polythiophene-based polyelectrolytes were prepared by simple quaternization reaction.•Polyelectrolytes with ammonium and phosphonium pendant groups were synthesized.•The effect of phosphonium and ammonium pendants on optical properties was assessed.•Fluorescence quenching by model...

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Bibliographic Details
Published in:European polymer journal 2018-03, Vol.100, p.200-208
Main Authors: Hladysh, Sviatoslav, Murmiliuk, Anastasiia, Vohlídal, Jiří, Havlíček, David, Sedlařík, Vladimír, Štěpánek, Miroslav, Zedník, Jiří
Format: Article
Language:English
Subjects:
Cationic polymerization
Chains (polymeric)
Chemical synthesis
Chloroform
Conjugated polyelectrolytes
Conjugated polymers
Electrolytes
Fluorescence
Light emitting diodes
Luminescence
NMR
Nuclear magnetic resonance
Photoluminescence quenching
Polyelectrolytes
Polymers
Polythiophene
Potassium ferricyanide
Prepolymers
Stern-Volmer constant
Transformations
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Summary:[Display omitted] •Polythiophene-based polyelectrolytes were prepared by simple quaternization reaction.•Polyelectrolytes with ammonium and phosphonium pendant groups were synthesized.•The effect of phosphonium and ammonium pendants on optical properties was assessed.•Fluorescence quenching by model pollutants was investigated using the Stern-Volmer method. A series of novel polythiophene-based cationic conjugated polyelectrolytes with phosphonium and ammonium pendants were prepared by modifying regioregular poly[3-(6-bromohexyl)thiophene] using a simple quaternization reaction with appropriate phosphine or amine. Partial transformation of the bromide end-groups of the polymer precursor with amine allowed adding the phosphine agent, thereby enabling quantitative transformation into a novel conjugated polyelectrolyte with phosphonium and ammonium groups in the same polymer main-chains. The properties of the synthesized polyelectrolytes in solution (water, methanol, DMSO and chloroform) were analyzed by UV/vis, luminescence, NMR, light scattering and TGA measurements. To test the prepared polyelectrolytes as potential luminescence sensors, fluorescence quenching measurements were performed in water, using K4[Fe(CN)6] and K3[Fe(CN)6] as quenchers. This study showed that polyelectrolytes containing both types of ionic pendant groups (phosphonium and ammonium) are more efficiently quenched.
ISSN:0014-3057
1873-1945
DOI:10.1016/j.eurpolymj.2018.01.029