Preparation and characterization of self assembled monolayers of 2-mercaptonicotinic acid on Au(111)

Pissinis, Diego Ezequiel; Pérez, Omar E. Linarez; Cometto, Fernando P.; Teijelo, M. López

doi:10.1016/j.jelechem.2013.11.013

Cited by 8 publications

(15 citation statements)

References 73 publications

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“…On the other hand, BT, MT, MNA, and MBA were used as representative ArTs, in which the aromatic group presents different functionalization, conferring different kinds of adlayer's structures. 30 In the case of ATs, the C* (the C atom directly bonded to the S atom) presents an sp 3 hybridization while in the ArTs, the C* presents an sp 2 hybridization. The influence of the C* hybridization on the binding energy of the AT versus ArT on both surfaces will be discussed later in this work.…”

Section: Resultsmentioning

confidence: 99%

“…In the case of aliphatic thiols, ATs with different chain lengths (C n T, n = 2, 3, 5, 6, 8, 9, 11, 12, and 16) were adsorbed from 0.2 mM ethanolic solutions on Au(111) and Au(100) surfaces. On the other hand, BT, MT, MNA, and MBA were used as representative ArTs, in which the aromatic group presents different functionalization, conferring different kinds of adlayer’s structures . In the case of ATs, the C* (the C atom directly bonded to the S atom) presents an sp 3 hybridization while in the ArTs, the C* presents an sp 2 hybridization.…”

Section: Resultsmentioning

confidence: 99%

“…Before the assembly process, both crystals were annealed in a hydrogen flame for two minutes, cooled under constant N 2 flux, and put in contact with water after one minute. 30 In the case of ATs, the C* (the C atom directly bonded to S atom) presents an sp 3 hybridization while in the ArTs, the C* presents an sp 2 hybridization. The influence of the C* hybridization on the binding energy of the AT vs ArT on both surfaces will be discussed later in this work.…”

Section: Experimental Methodsmentioning

confidence: 99%

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Comparative Study of the Adsorption of Thiols and Selenols on Au(111) and Au(100)

et al. 2017

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The effect of the Au crystalline plane on the adsorption of different thiols and selenols is studied via reductive desorption (RD) and X-ray photoelectron spectroscopy (XPS) measurements. Self-assembled monolayers (SAMs) using aliphatic (ATs) and aromatic thiols (ArTs) on both Au(111) and Au(100) were prepared. The electrochemical stability of these SAMs on both surfaces is evaluated by comparing the position of the RD peaks. The longer the AT chain the more stable the SAM on Au(100) when compared to Au(111). By means of XPS measurements, we determine that the binding energy (BE) of the S 2p signal corresponding to the S atoms at the thiol/Au interface, commonly assigned at 162.0 eV, shifts 0.2 eV from Au(111) to Au(100) for SAMs prepared using thiols with the C* (C atom bonded to S) in sp hybridization, such as ATs. However, when the thiol presents the C* with an sp hybridization, such as in the case of ArTs, the BE remains at 162.0 eV regardless of the surface plane. Selenol-based SAMs were characterized comparatively on both Au(100) and Au(111). Our results show that selenol SAMs become even more electrochemically stable on Au(100) with respect to Au(111) than the analogue sulfur-based SAM. According to our results, we suggest that the electronic distribution around the Au-S/Se bond could be responsible for the different structural arrangements reported in the literature (gold adatoms, etc.), which should be dependent on the crystalline face (Au(hkl)-S) and the chemical nature of the environment of the adsorbates (sp-C* vs sp-C* and Au-SR vs Au-SeR).

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Experimental Methodsmentioning

confidence: 99%

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Comparative Study of the Adsorption of Thiols and Selenols on Au(111) and Au(100)

et al. 2017

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“…3-/4-. 21,[27][28][29]32,50 The higher pK 1/2 app values found here for the MUA SAMs formed from a micellar medium may be partially related to favored intermolecular interactions due to a better organization and compactness. 51,52 However, the pK 1/2 app and intrinsic pK a values are still about 3−4 units higher than that of alkanoic acids in solution which cannot be easily accounted only by repulsive interactions as the 1 − pK model predicts.…”

Section: ■ Introductionmentioning

confidence: 69%

Influence of Patterning in the Acid–Base Interfacial Properties of Homogeneously Mixed CH₃- and COOH-Terminated Self-Assembled Monolayers

et al. 2018

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The acid/base interfacial behavior of mixed self-assembled monolayers (SAMs) of 1-decanethiol (DT) and 11-mercaptoundecanoic acid (MUA) formed on gold from a micellar medium has been characterized by electrochemical impedance spectroscopy (EIS) and infrared reflection–absorption spectroscopy (IRRAS) titration experiments as a function of their surface composition. The surface composition is determined from the interfacial capacitance of the SAMs that behave as a dielectric medium of the expected thickness for well-organized layers. The interaction parameter and the apparent and the intrinsic surface pK a values of these pH-responsive SAMs are obtained by fitting the EIS and IR titration curves to the 1-pK model. The shift in the surface pK a while decreasing the MUA surface fraction resembles the behavior of homogeneously mixed systems. The trends observed can be explained by the lowering of intermolecular in-plane repulsive interactions between neighboring MUA molecules and by the local solvation and hydrophobic effects when the MUA domains decrease below a critical size and the terminal groups are probably titrated at domain boundaries, small arrangements, or even isolated. The transition between both scenarios and the formation of hydrogen bonding interactions upon a structural reorganization are conditioned by the heterogeneity in the size distribution of MUA and DT molecular domains which depends on the formation conditions of the SAMs. All together it is demonstrated to play a role in the acid/base properties of these monolayers which has a direct implication in the proper design of interfacial devices based on organic molecular junctions or biomolecular assemblies.

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“…Adsorbates such as n ‐alkanethiols and their derivatives, 4,5 1,1‐dithiocarboxylates, 4,6,7 1,1‐dithiocarbamates, 4,8–10 and xanthates 4,11 have been used to synthesize SAM on Au(111) with acceptable stability. More information regarding the use of monodentate and multidentate organosulfur derivatives with different molecular architectures 12–16 is continually being reported. Studies on phosphorus‐containing adsorbates, particularly using bidentate 1,1‐dithio‐derivatives (i.e., those containing tetrahedral R 2 P(S)SH headgroups) have been explored 17–24 .…”

Section: Introductionmentioning

confidence: 99%

4,5‐Bis(diphenylthiophosphinoyl)‐1,2,3‐triazolate interaction with gold nanoparticles and flat surfaces to form self‐assembled monolayers

Correa‐Ascencio

Galván‐Miranda

Garcı́a-Montalvo

et al. 2020

Surface & Interface Analysis

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The interaction of the 4,5-bis(diphenylthiophosphinoyl)-1,2,3-triazolate (SPTz −) with different gold surfaces was investigated (nanoparticles, an electrode, and flat sheets). Studies on binding affinity of this dithiophosphin-triazolate on a gold electrode were performed by cyclic voltammetry (CV). Voltammograms exhibit two reductive desorption and only one oxidative readsorption, indicating that once reabsorbed, the molecule achieves a unique conformation. The morphology and average size of modified gold nanoparticles were studied by transmission electron microscopy (TEM) (av. diameter of 5.9 ± 1.8 nm). Further characterization was made by UV-visible (UV-vis) spectroscopy showing surface plasmon resonance (SPR) at about 580 nm. The bonding configurations of SPTz − on gold have also been investigated by comparing the FT-IR and FT-Raman spectra. The 31 P{ 1 H} NMR spectrum of capped nanoparticles exhibited two sharp signals at 30.3 and 29.6 ppm and a very broad signal at 72.7 ppm. X-ray photoelectron spectroscopy (XPS) showed SPTz − can accomplish a strong interaction with gold nanoparticles through bonds involving a sulfur atom and a nitrogen from the triazole ring with a free terminal PS group, forming self-assembled monolayers (SAM). This may allow subsequent functionalization through free S/N atoms of the formed SAMs. The SPTz − packing led to a reduction in packing density that permits large spaces between adsorbed headgroups and the inclusion of carbon and oxygen impurities from small molecules; nevertheless, oxidized sulfur or nitrogen species were not detected, indicating the chemical stability of the obtained SAMs.

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Preparation and characterization of self assembled monolayers of 2-mercaptonicotinic acid on Au(111)

Cited by 8 publications

References 73 publications

Comparative Study of the Adsorption of Thiols and Selenols on Au(111) and Au(100)

Comparative Study of the Adsorption of Thiols and Selenols on Au(111) and Au(100)

Influence of Patterning in the Acid–Base Interfacial Properties of Homogeneously Mixed CH₃- and COOH-Terminated Self-Assembled Monolayers

4,5‐Bis(diphenylthiophosphinoyl)‐1,2,3‐triazolate interaction with gold nanoparticles and flat surfaces to form self‐assembled monolayers

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Preparation and characterization of self assembled monolayers of 2-mercaptonicotinic acid on Au(111)

Cited by 8 publications

References 73 publications

Comparative Study of the Adsorption of Thiols and Selenols on Au(111) and Au(100)

Comparative Study of the Adsorption of Thiols and Selenols on Au(111) and Au(100)

Influence of Patterning in the Acid–Base Interfacial Properties of Homogeneously Mixed CH3- and COOH-Terminated Self-Assembled Monolayers

4,5‐Bis(diphenylthiophosphinoyl)‐1,2,3‐triazolate interaction with gold nanoparticles and flat surfaces to form self‐assembled monolayers

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Influence of Patterning in the Acid–Base Interfacial Properties of Homogeneously Mixed CH₃- and COOH-Terminated Self-Assembled Monolayers