Interfacial Hydrogen Bonding. Self-Assembly of a Monolayer of a Fullerene−Crown Ether Derivative on Gold Surfaces Derivatized with an Ammonium-Terminated Alkanethiolate

Arias, Francisco J.; Godı́nez, Luis A.; Wilson, Stephen R.; Kaifer, Ángel E.; Echegoyen, Luis

doi:10.1021/ja960445g

Cited by 151 publications

(124 citation statements)

References 16 publications

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“…Compounds 1a-1d were directly synthesized in high yield by reacting the corresponding bis-alcohols with thioctic acid in the presence of 1,3-dicyclohexylcarbodiimide (DCC) and 4-(dimethylamino) pyridine (DMAP), using CH 2 Cl 2 as solvent (10)(11)(12)(13)(14)(15)(16)(17)(18). The corresponding crown-annelated TTF bis-alcohol precursors were prepared in reasonable yields following a modification of the literature procedures (28,29,46).…”

Section: Resultsmentioning

confidence: 99%

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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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Section: Resultsmentioning

confidence: 99%

“…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)(11)(12)(13)(14)(15)(16)(17)(18).…”

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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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“…These values of C60 surface coverage were more larger than that previously reported . 2,7,23) Considering the first redox wave of C60 was not appeared (Fig. 3), the second reduction wave on cyclic voltammograms of C60／n／ITO electrodes might be due either to a twoelectron one-step reduction or to a broad mixed peak area of the first and the second reduction steps of immobilized C60 in this cases.…”

Section: ．Results and Discussionmentioning

confidence: 85%

Preparation and Photoelectrochemical Properties of Fullerene Modified ITO Electrodes Using Self-Assembled Monolayer

Ozawa

2004

Journal of The Surface Science Society of Japan

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Fullerene (C60) immobilized indium-tin-oxide (ITO) electrodes were prepared by a technique of self-assembled monolayers (SAMs) using five compounds of alkyldiamine (NH2(CH2)nNH2; n＝4, 6, 8, 10 and 12). These C60／diamine-SAMs modified ITO (C60／n／ITO; n＝4,6,8, 10 and 12) electrodes were examined in terms of properties of electrochemical and photoelectrochemical responses. The C60 surface coverage of C60／n／ITOs estimated was ca. 3×10 -10 to 4×10 -10 mol cm -2 . The stable anodic photocurrent appeared immediately after the irradiation of the C60／n／ITO electrode in 0.1 M Na2SO4 containing 50 mM ascorbic acid (AA) as an electron sacrificer with λ ＝400-600 nm, light power of 4.0-6.5 mW cm -2 and electrode potential of -0.15 V to ＋0.15 V vs. Ag／AgCl (saturated KCl). The photocurrents generated by C60／ n／ITOs increased with the number of the methylene unit (n) except for n＝12. These results have shown that increasing the length of the methylene contributes to only immobilization of C60, because of highly ordered structure of diamine-SAMs. 1．Introductionety onto ITO , 8) gold 9) surfaces have been reported previously. Because diamine show pronounced reacRecently , many researchers have studied on tivity to both C60 and ITO, they have been employed fullerene (C60) thin films formed using a variety of as prelayer of immobilized C60. cells, 10, 11) methods as Langmuir-Blodgett (LB) techniques and Organic-based photovoltaic which evaporation. 1) These C60 thin films have exhibited inmimic photoinduced multistep electron transfer procteresting electrochemical, photochemical and optical esses in photosynthesis, 12～14) have been developed in properties. However , the instability and the defect recent years. Photosynthesis is among the most charhave disadvantaged practical application of these sysacteristic examples of complicated molecular assemtems to molecular devices . Similarly , these phyblies in nature. In the photosynthesis system, followsisorbed fullerene thin films lack the stability and ing mutistep electron transfer takes place from the diuniformity at the nano-scale level . Several studies mer of chlorophyll to the quinines along the wellhave previously reported C60-containing selfarranged pigments fixed in the protein matrix, leadassembled monolayers (SAMs) immobilized onto the ing to the generation of a long-lived , chargesurfaces of gold , 2～4) indium-tin-oxide ( ITO ) 5) and separated state with nearly 100 ％ quantum yield . silicon dioxide. 6) SAMs are an interesting method forThe importance of molecular aggregates in nature has constructing highly ordered and densely packed encouraged us to assemble function molecules in artistructures on substrates. But, synthesis and preparaficial manner without the assist of protein. Covalent tion of self-assembling compounds linkage with the attachment of functional molecules to the terminal of C60 moiety was very arduous. Therefore, another apSAMs has been pursued to construct well-organized proach for immobilization of C60 onto the ITO surmolecular assemblies containing p...

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“…Chronoamperometry and amperometry techniques were largely used to measure the current and catalytic current generated by applying certain potentials and time during the immunosensors construction and immnunosensors assay (Martins et al, 2003;Ferreira et al, 2005;Zacco et al, 2006;Panini et al, 2008;Pividori et al, 2009). Square wave voltammetry (SWV) and differential pulse voltammetry (DPV) as analysis techniques are much more sensitive than cyclic voltammetry and amperometry mainly due to the elimination of the background current during the experiment course and for this reason they are frequently used in immunosesors assay (Arias et al, 1996;Wang & Tan, 2007;Tang & Xia, 2008;Yang et al, 2009). The measurements of electrical resistances or conductance (Tang & Xia, 2008;Maeng et al, 2008) have also been used to characterize immunosensors and in immunosensors assay.…”

Section: Other Electrochemical Techniquesmentioning

confidence: 99%

Preparation and Characterization of Imunosensors for Disease Diagnosis

Ferreira¹,

Fugivara²,

Yamanaka³

et al. 2011

Biosensors for Health, Environment and Biosecurity

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Interfacial Hydrogen Bonding. Self-Assembly of a Monolayer of a Fullerene−Crown Ether Derivative on Gold Surfaces Derivatized with an Ammonium-Terminated Alkanethiolate

Cited by 151 publications

References 16 publications

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

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

Preparation and Photoelectrochemical Properties of Fullerene Modified ITO Electrodes Using Self-Assembled Monolayer

Preparation and Characterization of Imunosensors for Disease Diagnosis

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