Redox-active monomeric and polymeric surfactants

Anton, P.; Heinze, J.; Laschewsky, André

doi:10.1021/la00025a019

Cited by 48 publications

(49 citation statements)

References 2 publications

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“…Figure 18 presents two systems, which seem to behave well. One is based on viologene as redox-active moiety, where the reduced state is zwitterionic [448][449][450]. The other one is based on ferrocene, where the oxidized state is zwitterionic [451,452].…”

Section: Responsive Polyzwitterionsmentioning

confidence: 99%

Structures and Synthesis of Zwitterionic Polymers

2014

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Abstract:The structures and synthesis of polyzwitterions ("polybetaines") are reviewed, emphasizing the literature of the past decade. Particular attention is given to the general challenges faced, and to successful strategies to obtain polymers with a true balance of permanent cationic and anionic groups, thus resulting in an overall zero charge. Also, the progress due to applying new methodologies from general polymer synthesis, such as controlled polymerization methods or the use of "click" chemical reactions is presented. Furthermore, the emerging topic of responsive ("smart") polyzwitterions is addressed. The considerations and critical discussions are illustrated by typical examples.

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Section: Responsive Polyzwitterionsmentioning

confidence: 99%

Structures and Synthesis of Zwitterionic Polymers

2014

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“…After 2 h, the reaction mixture was diluted with dichloromethane and washed with water and brine. The organic layer was dried over MgSO 4 and concentrated in vacuo to give a light yellow oil, which was used in the next step without further purification (0.59 g, 97%). Synthesis of 1H,1H,2H,2H,3H,3H-Perfluoroundecyltripropargylammonium Triflate.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Protection/Deprotection of Surface Activity and Its Applications in the Controlled Release of Liposomal Contents

Zhao

2012

Langmuir

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The micelles of two tripropargylammonium-functionalized cationic surfactants were cross-linked by a disulfide-containing diazido cross-linker in the presence of Cu(I) catalysts. With multiple residual alkyne groups on the surface, the resulting surface cross-linked micelles (SCMs) were postfunctionalized by reaction with 2-azidoethanol and an azido-terminated poly(ethylene glycol), respectively, via the alkyne-azide click reaction. The water-soluble nanoparticles obtained had low surface activity due to the buried hydrophobic tails. Cleavage of the disulfide cross-links by dithiothreitol (DTT) exposed the hydrophobic tails and resumed surface activity of the "caged" surfactants within 2 min after DTT addition. The controlled breakage of the SCMs was used to lower the surface tension of aqueous solutions and trigger the release of liposomal contents on demand. Disciplines Chemistry CommentsReprinted (adapted) with permission from Langmuir 28 (2012) ABSTRACT: The micelles of two tripropargylammoniumfunctionalized cationic surfactants were cross-linked by a disulfidecontaining diazido cross-linker in the presence of Cu(I) catalysts. With multiple residual alkyne groups on the surface, the resulting surface cross-linked micelles (SCMs) were postfunctionalized by reaction with 2-azidoethanol and an azido-terminated poly(ethylene glycol), respectively, via the alkyne−azide click reaction. The water-soluble nanoparticles obtained had low surface activity due to the buried hydrophobic tails. Cleavage of the disulfide cross-links by dithiothreitol (DTT) exposed the hydrophobic tails and resumed surface activity of the "caged" surfactants within 2 min after DTT addition. The controlled breakage of the SCMs was used to lower the surface tension of aqueous solutions and trigger the release of liposomal contents on demand.

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“…Similar to other viologen-containing polysoaps [3], a change in the oxidation state of P-1 leads to a drastic change of its solubility. The question arises if such an effect can be used to control other properties of polysoaps, e.g.…”

Section: Introductionmentioning

confidence: 93%

“…N. Kuramoto et al demonstrated that the lower critical solution temperature of poly(Nacryloylpyrrolidine-co-vinylferrocene) depends on the concentration and oxidation state of the ferrocene moieties [2]. Recently, we synthesized a series of redox-active micellar polymers, whose solubility can reversibly be influenced by a redox moiety [3]. We were now interested in further consequences of the redox state on the polysoap properties.…”

Section: Introductionmentioning

confidence: 99%

“…cast films and Langmuir-Blodgett films [6]. Noteworthy, the cyclic voltammograms of P-2 and its acrylate homologue are almost identical with respect to their shape and position of the peak potentials [3], Reversibility of the redox reaction and adsorption of the reduced species was examined more closely with an electrochemical quartz crystal microbalance (EQCM). This method relies on the frequency decrease of a quartz crystal bearing a gold electrode, when redoxactive molecules are electro-deposited on its surface [7].…”

Section: Introductionmentioning

confidence: 99%

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Solubilization control by redox-switching of polysoaps

1995

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SummaryReversible changes in the self-organization of polysoaps may be induced by controlling their charge numbers via covalently bound redox moieties. This is illustrated with two viologen polysoaps, which in response to an electrochemical stimulus, change their solubility and aggregation in water, leading from homogeneously dissolved and aggregated molecules to collapsed ones and vice verse. Using the electrochemical quartz crystal microbalance (EQCM), it could be shown that the reversibility of this process is better than 95% in 16 cycles. IntroductionMonomelic and polymeric surfactants that respond to external stimuli such as temperature, electrical charge or irradiation with light offer the possibility of controlling surfactant properties such as solubility, solubilization capacity or emulsification properties right on the spot. As examples, Saji et al. could disintegrate micelles of low molecular weight ferrocene surfactants by oxidation. Thin films of hydrophobic compounds that had been solubilized by these surfactants were thus deposited onto the electrode surface [1]. N. Kuramoto et al. demonstrated that the lower critical solution temperature of poly(Nacryloylpyrrolidine-co-vinylferrocene) depends on the concentration and oxidation state of the ferrocene moieties [2]. Recently, we synthesized a series of redox-active micellar polymers, whose solubility can reversibly be influenced by a redox moiety [3]. We were now interested in further consequences of the redox state on the polysoap properties. In this context, two viologen polysoaps P-l and P-2 (Fig. 1) were investigated in more detail.

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Redox-active monomeric and polymeric surfactants

Cited by 48 publications

References 2 publications

Structures and Synthesis of Zwitterionic Polymers

Structures and Synthesis of Zwitterionic Polymers

Protection/Deprotection of Surface Activity and Its Applications in the Controlled Release of Liposomal Contents

Solubilization control by redox-switching of polysoaps

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