Surfactant monolayers on electrode surfaces: self-assembly of a series of amphiphilic viologens on gold and tin oxide

Gomez, Marielle E.; Li, Jing; Kaifer, Ángel E.

doi:10.1021/la00056a037

Cited by 68 publications

(38 citation statements)

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“…The viologen precursor was prepared from 4, 4'-bipyridine with bromoethane and 3-bromopropionic acid in benzene. 29 Dendrimers were modified with the viologens according to the EDC/NHS coupling procedure by Vijay, et al 30 Scheme 1 outlines the synthetic sequence. An aqueous solution (5 mL) of NHS (150 mg) and viologen precursor (400 mg) was stirred for 1 h at 0 °C.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Characterization, and Electrochemical Behavior of Viologen-Functionalized Poly(Amidoamine) Dendrimers

Oh¹,

Bae²,

Yoon³

et al. 2004

Bulletin of the Korean Chemical Society

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Amineterminated, ethylenediamine core polyamidoamine starburst dendrimers of generation 2 (G2), generation 4 (G4) and generation 6 (G6) have been successfully surface-modified via an amide coupling reaction with 4-ethyl, 4'-(3-propionic) bipyridinium cation and the electrochemical behavior of the resulting dendrimers were investigated in aqueous potassium chloride electrolyte solutions. The 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride/N-hydroxysuccinimide-mediated reaction resulted in 25-39% end-group functionalization. The water-soluble 4-ethyl, 4'-(3-propylamide) bipyridinium dibromide dendrimers (G2-V2+, G4-V2+ and G6-V2+) were characterized by 1 H NMR and UV-Vis spectroscopic methods. The cyclic voltammetric and chronoamperometric experiments were performed to determine the diffusion coefficient and the number of electrons transferred in the process of the first reduction of the viologen-functionalized dendrimers. Adsorption of viologen-functionalized dendrimers at electrode surface was evidenced in the voltammograms. Experimentally determined diffusion coefficients were in good agreement with the values expected from the Stokes-Einstein relation, while the number of electrons transferred concurred with the extent of functionalization determined by 1 H NMR and UV-Vis spectra.

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Section: Methodsmentioning

confidence: 99%

Synthesis, Characterization, and Electrochemical Behavior of Viologen-Functionalized Poly(Amidoamine) Dendrimers

Oh¹,

Bae²,

Yoon³

et al. 2004

Bulletin of the Korean Chemical Society

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“…22 Amphiphilic molecules are known to aggregate on solid surfaces such as tin oxide and gold. 23 A graphite surface is also known to adsorb surfactants. 24 Therefore, the effects of a cation surfactant cetyltrimethylammonium bromide (CTAB), the anionic surfactant sodium dodecyl sulfate (SDS) and the nonionic surfactant Triton X-100 on the stripping voltammetric 1589 ANALYTICAL SCIENCES DECEMBER 2003, VOL.…”

Section: Effect Of Surfactantsmentioning

confidence: 99%

Determination of Trace Procaine Hydrochloride by Differential Pulse Adsorptive Stripping Voltammetry with a Nafion Modified Glassy Carbon Electrode

Duan

2003

ANAL. SCI.

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Procaine hydrochloride is a local anaesthetic, which is widely used for injections and for local applications to mucous membranes. It produced a reversible loss of sensation by diminishing the conduction of sensory nerve impulses near to the site of the application or injection. 1 The United States, British and Chinese pharmacopoeia methods for assaying procaine are based on the solvent extraction of procaine hydrochloride, followed by a spectrophotometric measurement, titration with sodium hydroxide, or dead-stop titration. [2][3][4] Other techniques, such as high-performance liquid chromatography, 5 gas chromatography, 6 chemiluminescence, 7,8 fluorometry, 9,10 ultraviolet-visible spectrophotometry 11 and electrochemistry, [12][13][14] have been used for determining procaine. However, most of them require several time-consuming manipulation steps, sophisticated instruments and special training. Some of these methods suffer from poor sensitivity. There is a constant demand for improved analytical methods for the sensitive and selective determination of procaine hydrochloride in biological and medical fields. Chemically modified electrodes are an active research area in many aspects of science and technology, having potential applications in diverse fields. [15][16][17] Nafion is a good cation-exchanger with advantages of chemical inertness, thermal stability and mechanical strength, and is widely used to modify electrodes in electrochemistry. 18,19The hydrophilic negatively charged sulfonate group in Nafion enables it to selectively preconcentrate cations by electrostatic interaction, whereas, the hydrophobic fluorocarbon network of the polymer gives it ionic selectivity for hydrophobic organic cations by a hydrophobic interaction. These two factors give Nafion selectivity for cations, and especially high selectivity for hydrophobic organic cations. 20 This paper presents a new method for the determination of procaine hydrochloride by differential pulse adsorptive stripping voltammetry with a Nafion-modified electrode. The proposed method is the most sensitive among those reported. The detection limit is 7.0 × 10 -9 mol l -1 with 180 s accumulation. The method has been successfully applied to the determination of procaine hydrochloride in an injection solution and in rabbit serum with satisfactory results. Experimental ApparatusA CHI 660A Electrochemical Workstation (CHI Instruments) was used for electrochemical measurements. A conventional three-electrode system was employed with a Nafion-modified electrode (3.0 mm in diameter) as the working electrode, a platinum wire as an auxiliary electrode, and a saturated calomel electrode (SCE) as a reference electrode. All potentials reported in this paper were referenced to the SCE. A sensitive and selective method for the determination of procaine hydrochloride with a Nafion-modified glassy carbon electrode has been developed. The voltammetric behavior of procaine hydrochloride on the Nafion-modified electrode indicated that the modified electrode not only increased ...

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“…Electrodes not exhibiting the reversible response of the redox couple with peak to peak separation Ϸ60 mV were discarded. The geometric area of the electrode (typically 0.2-0.4 cm 2 ) was obtained from the slope of a linear plot of the cathodic current versus (scan rate) 1/2 for the reversible reduction of the above-mentioned redox probe, taking 7.5 ϫ 10 Ϫ6 cm 2 ͞s as the diffusion coefficient, and knowing the exact concentration from the mass (40). The gold substrates for reflection-absorption infrared spectroscopy (RAIR) are prepared by vacuum deposition of gold (at a pressure of Ϸ10 Ϫ7 Torr) on glass microslides coated with 3 mercaptotrimethoxysilane for better adhesion (41).…”

mentioning

confidence: 99%

Metal ion recognition and molecular templating in self-assembled monolayers of cyclic and acyclic polyethers

Herranz

Colonna

Echegoyen

2002

Proc. Natl. Acad. Sci. U.S.A.

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Our recent work with cyclic and acyclic polyether self-assembled monolayers (SAMs) on gold is presented. A series of dithia-crowntetrathiafulvalene derivatives with one or two disulfide groups has been prepared, and their SAMs on gold have been characterized by electrochemistry and by reflection-absorption infrared spectroscopy. These SAMs are extremely stable on repeated electrochemical potential scans and can selectively recognize alkali metal ions. Acyclic polyether derivatives can also self-assemble on gold to yield selective metal ion recognition domains. Impedance spectroscopy data for these SAMs fit the Langmuir isotherm and allow the determination of ion association constants. Some of the SAMs prepared with new acyclic polyether derivatives are able to detect potassium cations selectively when templated in their presence. These structures are believed to be a consequence of ion ''imprinting'' during the process of SAM formation.T he easy preparation, stability, and versatility of self-assembled monolayers (SAMs) has resulted in considerable activity in this field since the first publication by Nuzzo and Allara (1). Molecular recognition is especially relevant on surfaces because it allows the control of the exchange of signals, structures, and energy through the interfaces (2-4). SAMs allow the introduction of functional groups in the adsorbates, thus offering a powerful way to develop systems that have applications as sensors, devices, and switches (5). Some recent articles have reported surface structures with hydrophobic and hydrophilic properties arranged in nano-strips and honeycomb or homogeneous structures (6), whereas others have detected photo and electrochemical conversion of cis to trans forms within the SAM (7). Other examples have shown the formation of chiral imprinted sites (8). SAM structures have also been prepared for the recognition and sensing of metal ions (9), some of which are electrochemically active (10-18).Relatively recently, and Bryce et al. (23,24) reported, almost simultaneously, the incorporation of crownether groups into SAMs and their use as potential metal ion sensors. The Reinhoudt group used electrochemical impedance spectroscopy (EIS) for SAM characterization and to study the ion recognition processes (19)(20)(21)(22). This technique enables the detection of interfacial ion recognition phenomena when both guest ion and host monolayer are electrochemically inactive, by detecting changes of the charge-transfer resistance induced by metal ion binding (see Fig. 1a; refs. 25 and 26). The report by Bryce et al. (23,24) described SAMs of crown-annelated tetrathiafulvalene (TTF) derivatives, which showed, by cyclic voltammetry (CV), a redox potential shift of the electroactive, surface-confined, crown-TTF group on ion complexation (23, 24). The first TTF-crown SAMs reported by this group were apparently unstable after several electrochemical scans (23). However, in a subsequent report they demonstrated that the stability and electrochemical behavior of the SAMs can be improv...

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Surfactant monolayers on electrode surfaces: self-assembly of a series of amphiphilic viologens on gold and tin oxide

Cited by 68 publications

References 1 publication

Synthesis, Characterization, and Electrochemical Behavior of Viologen-Functionalized Poly(Amidoamine) Dendrimers

Synthesis, Characterization, and Electrochemical Behavior of Viologen-Functionalized Poly(Amidoamine) Dendrimers

Determination of Trace Procaine Hydrochloride by Differential Pulse Adsorptive Stripping Voltammetry with a Nafion Modified Glassy Carbon Electrode

Metal ion recognition and molecular templating in self-assembled monolayers of cyclic and acyclic polyethers

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