Formation of Well-Defined<i>p-tert</i>-Butylcalix[4]arenedithiolate Monolayers on a Au(100)−(1 × 1) Surface Studied by In Situ Scanning Tunneling Microscopy

Abe, Mitsunari; Itaya, Kingo; Narumi, Fumitaka; Sashikata, K.; Nishiyama, Katsuhiko; Taniguchi, Ikuo

doi:10.1021/la034819c

Cited by 11 publications

(12 citation statements)

References 39 publications

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“…Yoshimoto et al also immobilized p -tert-butylcalix[4]arene-1,3-dithiol (BCAD) on a Au(100) surface. The two sulfurs of BCAD are assumed to be located on the near 2-fold bridging site on the basis of the distances between the molecules and the molecular orientation observed in the STM images …”

Section: Resultsmentioning

confidence: 99%

STM Study on Nonionic Fluorosurfactant Zonyl FSN Self-Assembly on Au(100): (3−111) Molecular Lattice, Corrugations, and Adsorbate-Enhanced Mobility

et al. 2010

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Nonionic fluorosurfactant zonyl FSN self-assembly on Au(100) is investigated by using scanning tunneling microscopy under ambient conditions. High-resolution STM images reveal that a [array: see text] arrangement of the FSN SAMs is formed on Au(100). Different from the uniform structure of FSN SAMs on Au(111), the adsorption sites of FSN molecules on Au(100) change gradually and form a kind of corrugated structure. The change in the adsorption sites probably originates from the repulsive force among FSN molecules because the nearest-neighbor distance of FSN molecules is 0.41 nm, which is smaller than 0.50 nm on Au(111). The mobility of surface atoms on the Au substrate is enhanced by the interaction between FSN molecules and the Au substrate; therefore, no Au island is observed on the FSN-SAM-covered Au(100).

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Section: Resultsmentioning

confidence: 99%

STM Study on Nonionic Fluorosurfactant Zonyl FSN Self-Assembly on Au(100): (3−111) Molecular Lattice, Corrugations, and Adsorbate-Enhanced Mobility

et al. 2010

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“…On the basis of the STM image described above, we tentatively assigned the unit cell defined in Fig. 5b 95 It is noteworthy that no highly ordered adlayer of BCAD was seen on the terrace when Au(111) was used as the substrate. The preliminary result suggests that the structure of chemisorbed BCAD layer depends upon the crystallographic orientation of Au.…”

Section: -Pys (44mentioning

confidence: 97%

Molecular Assemblies of Functional Molecules on Gold Electrode Surfaces Studied by Electrochemical Scanning Tunneling Microscopy: Relationship between Function and Adlayer Structures

Yoshimoto

2006

Bulletin of the Chemical Society of Japan

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In this research, molecular assembly and function of aromatic thiols, porphyrins, phthalocyanines, and fullerenes on gold single crystal surfaces was studied by electrochemical methods and scanning tunneling microscopy (STM). Surface functions of promoter molecules such as pyridinethiols, pyrimidinethiols, and benzenethiol for cytochrome c electrochemistry were characterized by electrochemical techniques. Adlayer structures of those molecules were investigated by in situ STM, and molecular orientations for each molecule on the Au surfaces were clarified at molecular level. Adlayers of porphyrins and phthalocyanines for electrocatalytic reduction of dioxygen were examined to elucidate the relationship between activity and adlayer structure. Stable two-dimensional arrays of cobalt porphyrins indicated two-electron reduction of O 2 to H 2 O 2 , whereas two-step four-electron reduction of O 2 to H 2 O occurred because of highly mobile porphyrinatoiron molecules on the surface. Furthermore, well-defined adlayers of crown-substituted phthalocyanine for host-guest interface and binary array consisting of porphyrin and phthalocyanine for the design of supramolecular nanoarchitectures were clearly visualized by STM. Finally, a unique approach for controlling molecular orientation was found by the formation of supramolecular assemblies consisting of porphyrin and fullerene. The electrochemical redox reaction of carbonyl and ferrocene moieties was promoted by using the simple method for the construction of a 1:1 supramolecular assembled film consisting of C 60 derivative and octaethylporphyrinatometal on Au single crystal surfaces.In the field of electrochemistry, surface modification is often used for controlling electron-transfer reactions and catalytic activity. Especially, the electron-transfer reaction of a metalloprotein is currently one of the most active areas in bioelectrochemistry and related fields.

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“…For example, lipophilic dithiamercaptocalixarenes bearing C 12 alkyl chains have been used for the extraction of mercury from aqueous solutions, [23] and the formation of well-defined mono-layers of mercaptocalix [4]arenes on Au surface has also been described. [24] Finally, the detection of aromatics in aqueous solution by surface-enhanced Raman scattering using substrates chemically modified with p-tert-butyltetramercaptocalix [4]arene has also been investigated, [25] which further illustrates the interest of the calix [4]arene platform for the development of chemical sensors.…”

Section: Introductionmentioning

confidence: 99%

Expanded Mercaptocalixarenes: A New Kind of Macrocyclic Ligands for Stabilization of Polynuclear Thiolate Clusters

Schleife

Bonnot

Chambron

et al. 2022

Chemistry A European J

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The syntheses and properties of expanded 4‐tert‐butyl‐mercaptocalix[4]arenes, in which the methylene linkers are replaced by −CH2NRCH2− or −CH2NRCH2− and −CH2NRCH2CH2CH2NRCH2− units, are described. The new macrocycles were obtained in a step‐wise manner, utilizing fully protected, i. e. S‐alkylated, derivatives of the oxidation‐sensitive thiophenols in the cyclisation steps. Reductive cleavage of the macrobicyclic or macrotricyclic intermediates (6, 7, 11) afforded the free thiophenols (H48, H49, and H412) in preparative yields as their hydrochloride salts. The protected proligands can exist in two conformations, resembling the “cone” and “1,3‐alternate” conformations found for the parent calix[4]arenes. The free macrocycles do not show conformational isomerism, but are readily oxidized forming intramolecular disulfide linkages. Preliminary complexation experiments show that these expanded mercaptocalixarenes can serve as supporting ligands for tetranuclear thiolato clusters.

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Formation of Well-Definedp-tert-Butylcalix[4]arenedithiolate Monolayers on a Au(100)−(1 × 1) Surface Studied by In Situ Scanning Tunneling Microscopy

Cited by 11 publications

References 39 publications

STM Study on Nonionic Fluorosurfactant Zonyl FSN Self-Assembly on Au(100): (3−111) Molecular Lattice, Corrugations, and Adsorbate-Enhanced Mobility

STM Study on Nonionic Fluorosurfactant Zonyl FSN Self-Assembly on Au(100): (3−111) Molecular Lattice, Corrugations, and Adsorbate-Enhanced Mobility

Molecular Assemblies of Functional Molecules on Gold Electrode Surfaces Studied by Electrochemical Scanning Tunneling Microscopy: Relationship between Function and Adlayer Structures

Expanded Mercaptocalixarenes: A New Kind of Macrocyclic Ligands for Stabilization of Polynuclear Thiolate Clusters

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