Distinct self-assembly of dithiol monolayers on Au(111) in water and hexane

Sharif, Aisyah Mohamad; Laffir, Fathima; Buckley, D. H.; Silien, Christophe

doi:10.1016/j.chemphys.2014.06.019

Cited by 7 publications

(8 citation statements)

References 45 publications

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“…It is dominated by a doublet with S2p 3/2 binding energy (BE) of around 163.5 eV (denoted as III) that is attributed to sulfur as part of (unreacted) thiol groups . A second feature (II) is resolved at about 1 eV lower BE, which we assign to thiolate, that is, a thiol group bound to the gold under dehydrogenation . Its intensity appears distinctly lower as the thiolates are buried below the organic layer so that the emitted photoelectrons are attenuated.…”

Section: Resultsmentioning

confidence: 95%

“…By contrast, SAMs prepared from DCM solution reveal an additional sulfur species (denoted I) with a BE around 161 eV, which can be associated with sulfide species bond to the gold surface that are formed upon S‐C scission in the molecule. Alternatively, such signals have also been related to metastable thiolate species in different chemical situation (e.g., bound to defects) . Either way, it represents a lack in film quality as molecules may decompose prior to or while binding.…”

Section: Resultsmentioning

confidence: 99%

“…It illustrates the importance of working in oxygen and water free conditions and usage of dried and degassed solvents. Since conjugated molecules are prone to oxidation and due to their small bandgap also photooxidation may appear dark ambient is recommended …”

Section: Resultsmentioning

confidence: 99%

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Structure and Thermal Stability of Stilbenedithiol SAMs on Au(111)

Völkner

Bashir

Parak

2018

Physica Status Solidi (a)

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Self-assembling monolayers (SAMs) of dithiols play an important role as bivalent linker layer in applications such as photoelectrochemical sensors. However, their formation processes and film structure are not fully understood yet. Herein, a SAM of aromatic trans-stilbenedithiol (StDT) on Au(111) surfaces is investigated. Using complementary characterization techniques the dependence of the film quality on preparation parameters, such as used solvent, temperature and ambient conditions during and subsequent to preparation is investigated. Furthermore, a remarkably high thermal stability is found which is ascribed to disulfide bridging between the endgroups of the individual molecules.

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Section: Resultsmentioning

confidence: 95%

Section: Resultsmentioning

confidence: 99%

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Structure and Thermal Stability of Stilbenedithiol SAMs on Au(111)

Völkner

Bashir

Parak

2018

Physica Status Solidi (a)

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“…[11][12][13][14][15]30 In addition, aromatic thiols, such as 1,4benzenedimethanethiol molecules, also formed striped phases on gold at low coverages. 20 These striped phases exhibit longrange order or periodicity. [10][11][12][13]15,16,22 Within these structures, thiols lie down on Au surfaces, and the chain−surface and chain−chain van der Waals interactions provide a basis for the formation of various striped structures.…”

Section: Introductionmentioning

confidence: 99%

“…[10][11][12][13]15,16,22 Within these structures, thiols lie down on Au surfaces, and the chain−surface and chain−chain van der Waals interactions provide a basis for the formation of various striped structures. [10][11][12][13][14][15]20,23 Therefore, we hypothesized that the OPDT molecules would likely form striped structures at submonolayer coverages. By detaching a portion of the adsorbates with an OPDT SAM, we could create coexisting striped structures inlaid in the mature monolayer of OPDT SAM.…”

Section: Introductionmentioning

confidence: 99%

Molecular Level Structural Characterization of Self-Assembled Monolayers of Functionalized Bidentate Aromatic Thiols

et al. 2021

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While molecular-level structural information is readily available for n-alkanethiol self-assembled monolayers (SAMs) on noble metal surfaces, the same cannot be claimed for dithiol-based SAMs due to their lack of long-range-order. This work provides molecular-level structural information on dithiol SAMs by investigating 5-(octyloxy)-1,3-phenylenedimethanethiol (OPDT) SAMs on Au(111) surfaces, using combined high-resolution scanning tunneling microscopy (STM), atomic force microscopy (AFM), and nanolithography. The high coverage OPDT SAMs do not exhibit long-range order. Desorption of these OPDT SAMs leads to the formation of ordered domains known as the striped phases, whose unit mesh is revealed as commensurate with the underlying Au(111) lattice. In these domains, OPDT molecules are lying-down, with the benzene ring and the zigzag plane of the alkyl chain parallel to the Au(111) surface. At the boundaries of these ordered structures, standing-up OPDT molecules are frequently present with an intermolecular space of 1 nm (i.e., 1D ordered structures). Using these ordered structures as internal standards in situ, the structure of the high-coverage OPDT SAMs is revealed: a mixture of standing-up and lying-down molecules randomly distributed on Au(111); as such, these SAMs exhibit little long-range order or ordered domains. The two thiols of each OPDT molecule occupy triple hollow sites on Au(111) surfaces. In the standing-up configuration, the benzene ring is perpendicular to the surface. In the lying-down con-figuration, the benzene ring and zigzag plane of the alkyl chain are parallel to the Au(111) surface. This work represents a high-resolution and molecular-level structural characterization of functionalized dithiol SAMs, furthering our understanding of dithiol molecule−surface interactions and the unique properties of these SAMs.

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