Observations of image contrast and dimerization of decacyclene by low temperature scanning tunneling microscopy

Wesoloski, Lisa M.; Stieg, Adam Z.; Kunitake, Masashi; Dultz, Shane C.; Gimzewski, James K.

doi:10.1063/1.2799991

Cited by 4 publications

(7 citation statements)

References 58 publications

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“…Changes of intralayer corrugation with bias have been reported in different situations. 33,34 For single molecules, a corrugation change with bias was reported that disappeared when molecules dimerized. 33 This is clearly not the case here, where the corrugation change happens for the high-coverage case.…”

Section: ■ Discussionmentioning

confidence: 99%

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Adatom Coadsorption with Three-Dimensional Cyclophanes on Ag(111)

et al. 2017

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The structure of molecular adlayers is of great interest for surface functionalization. As molecular complexity increases, the subtle interplay of the relevant interactions becomes more difficult to unravel. Here, we present a scanning tunneling microscope (STM) and atomic force microscope study along with free-energy calculations using density functional theory on two closely related NDI-cyclophane molecules. These three-dimensional double-decker molecules are designed to attach to the substrate with one subunit while the other functional moiety is exposed to the environment. The molecular arrangements obtained on Ag(111) are rationalized by the inclusion of adatoms from the substrate into the structure. The presence of adatoms is identified by a drastic change in corrugation of the STM images that takes place at moderate bias voltages. Our calculations using density functional theory of the system’s free-energy yield that two adatoms favorably coadsorb with the molecules.

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Section: ■ Discussionmentioning

confidence: 99%

“…33,34 For single molecules, a corrugation change with bias was reported that disappeared when molecules dimerized. 33 This is clearly not the case here, where the corrugation change happens for the high-coverage case. Another case was due to picking-up oxygen atoms by the STM tip.…”

Section: ■ Discussionmentioning

confidence: 99%

Adatom Coadsorption with Three-Dimensional Cyclophanes on Ag(111)

et al. 2017

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“…Hydrogen atoms in the interior of the decacyclene unit sterically repel one another such that each naphthalene unit twists out of plane with respect to the central benzene ring, contorting the planar decacyclene core into either a 3D propeller or boat conformation. 32 The propeller conformation refers to the decacyclene core of HBDC having its naphthalene groups twist out of plane such that it resembles a propeller or the blades of a fan, and the boat conformation refers to the same propeller conformation but with one of the naphthalene groups twisted in the opposite direction such that it more closely resembles a boat. These flexible naphthalene units play a large role in the unique mechanical properties that are preserved after functionalization with tert-butyl units.…”

Section: ■ Methodsmentioning

confidence: 99%

“…Here, a false color scale is used to emphasize the highest tert-butyl lobes, where there is a difference of 0.2 Å between the top of the red-tipped lobes and the white layer. Although full monolayers of decacyclene are not chirally separated, 32,39 it is proposed that the addition of tert-butyl groups to HBDC serves to amplify the chirality of the decacyclene core and serves as the conduit through which chiral recognition occurs. At monolayer coverage, HBDC exists as enantiopure domains as shown in Figure 3b, where domains I and II are the enantiopure terrace domains, A00 and B00, described as in matrix notation, respectively.…”

Section: ■ Methodsmentioning

confidence: 99%

Amplification of Conformational Effects via tert-Butyl Groups: Hexa-tert-butyl Decacyclene on Cu(100) at Room Temperature

Pawin¹,

Stieg

Skibo³

et al. 2013

Langmuir

Self Cite

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The design of molecular systems as functional elements for use in next-generation electronic sensors and devices often relies on the addition of functional groups acting as spacers to modify adsorbate-substrate interactions. Although advantageous in many regards, these spacer groups have the secondary effect of amplifying internal conformational effects of the parent molecule. Here we investigate one such molecule-2,5,8,11,14,17-hexa-tert-butyl-decacyclene (HBDC, C60H66)-deposited on Cu(100) at monolayer and submonolayer coverages using an ultra-high vacuum (UHV) scanning tunneling microscope (STM). By combining submolecular resolution imaging with computational methods, we describe a variety of properties related to the effects of adding tert-butyl spacers to a decacyclene core, including the molecular conformation, structure, and chiral separation of the molecular adlayer, strong intermolecular interactions, and a metastable pinned conformation of the molecule brought on by deformation under high-bias conditions that enable an examination of its diffusive 2D molecular gas at room temperature. Collectively, these observations provide direct insight into the effect of adding spacers to a flexible molecular core such as decacyclene as relates to both intermolecular and adsorbate-substrate interfaces.

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“…The relative orientation of the molecules in these aggregates is therefore likely influenced by long-range dipole-dipole interactions, with hydrogen-bonding interactions further stabilizing the structure. Wesoloski et al [44] have revealed both monomer and dimer forms of decacyclene (DC) on atomically clean Cu(100) and Cu(111). They provide evidence of both dimer formation and dissociation and suggest that two DC molecules stack by aligning their molecular planes in a parallel fashion with respect to the surface.…”

Section: The Adsorption Configuration Of Ofms On Hopgmentioning

confidence: 99%

Adsorption characteristic of self‐assembled corrole dimers on HOPG

Miao

Gao

Hiroto

et al. 2009

Surface & Interface Analysis

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Our study first focus on two types of corrole dimers oxidized and reduced forms on highly oriented pyrolytic graphite (HOPG) surface. Scanning tunneling microscopy (STM), X-ray photoelectron spectroscopy (XPS) and contact angle measurement (CAM) were used to investigate the self-assembled monolayers of corrole dimers adsorbed on HOPG surfaces at room temperature in air. XPS and CAM results have confirmed both two molecules adsorbed on an HOPG surface and formed self-assembled films, and STM experiments found that the corrole dimers adsorbed on HOPG surfaces form similar lobes. The different stable space structure of the oxidized form molecule (OFM) and reduced form molecule (RFM), led to the diversity of the tetramer structural dimensions. The occurrence of molecular aggregations and assembly was controlled by the interactions between molecular-molecular and molecule-substrate. The electrostatic interactions between the molecules control the geometrical sizes and molecule-substrate interactions determine topographical shapes of the self-assembled corrole dimers on HOPG surface.

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Observations of image contrast and dimerization of decacyclene by low temperature scanning tunneling microscopy

Cited by 4 publications

References 58 publications

Adatom Coadsorption with Three-Dimensional Cyclophanes on Ag(111)

Adatom Coadsorption with Three-Dimensional Cyclophanes on Ag(111)

Amplification of Conformational Effects via tert-Butyl Groups: Hexa-tert-butyl Decacyclene on Cu(100) at Room Temperature

Adsorption characteristic of self‐assembled corrole dimers on HOPG

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