Adsorption of Aldehydes on a Graphite Substrate: Combined Thermodynamic Study of C6−C13 Homologues with a Structural and Dynamical Study of Dodecanal

Phillips, Tamsin K.; Bhinde, Tej; Clarke, Stuart M.; Lee, Seung Y.; Mali, Kunal S.; Feyter, Steven De

doi:10.1021/jp911069t

Cited by 22 publications

(19 citation statements)

References 54 publications

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“…However, the Moiré pattern or in general, any contrast variation that arises due to specific registry effects on the HOPG surface, is periodic and thus can be easily identified. In fact, due to its periodic appearance, the Moiré pattern has been used to calculate intermolecular distances with accuracy 15c. In the case of Pb‐Pyc , however, the appearance of bright and dark molecules is not periodic, thus ruling out this possibility.…”

Section: Resultsmentioning

confidence: 99%

Manifestations of Non‐Planar Adsorption Geometries of Lead Pyrenocyanine at the Liquid‐Solid Interface

Mali

Zöphel

Ivasenko

et al. 2013

Chemistry An Asian Journal

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In this work, we provide evidence for multiple non-planar adsorption geometries of a novel pyrenocyanine derivative at the liquid-solid interface under ambient conditions. When adsorbed at the organic liquid-solid interface, lead pyrenocyanine forms well-ordered monolayers that exhibit peculiar non-periodic contrast variation. The different contrast of the adsorbed molecules is attributed to dissimilar adsorption geometries which arise from the non-planar conformation of the molecules. The non-planarity of the molecular backbone in turn arises due to a combination of the angularly extended pyrene subunits and the presence of the large lead ion, which is too big to fit inside the central cavity and thus is located out of the aromatic plane. The two possible locations of the lead atom, namely below and above the aromatic plane, could be identified as depression and protrusion in the central cavity, respectively. The manifestation of such multiple adsorption geometries on the structure of the resultant monolayer is discussed in detail. The packing density of these 2D arrays of molecules could be tuned by heating of the sample wherein the molecular packing changes from a low-density, pseudo six-fold symmetric to a high-density, two-fold symmetric arrangement. Finally, a well-ordered two-component system could be constructed by incorporating C60 molecules in the adlayer of lead pyrenocyanine at the liquid-solid interface.

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Section: Resultsmentioning

confidence: 99%

Manifestations of Non‐Planar Adsorption Geometries of Lead Pyrenocyanine at the Liquid‐Solid Interface

Mali

Zöphel

Ivasenko

et al. 2013

Chemistry An Asian Journal

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“…It has previously been shown that a difference in registry with an underlying surface can lead to changes in contrast of molecules imaged by STM (and is generally accepted as the cause of the often observed moiré patterns in a molecular layer on top of graphite). 36,41,42 In fact, some research groups use the difference in contrast as a way to quantify the mismatch of adsorbed molecules with the registry of the underlying graphite. 43 We therefore propose that this is the explanation for the observed contrast differences for AuC12 and AuC18.…”

Section: Contrast Differences In Stm Topographymentioning

confidence: 99%

STM Study of Gold(I) Pyrazolates: Distinct Morphologies, Layer Evolution, and Cooperative Dynamics

et al. 2013

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We describe the first study of trinuclear gold(I) pyrazolates on the molecular level by timedependent Scanning Tunneling Microscopy (STM). On the graphite/1-octanoic acid interface dodecyl functionalized gold pyrazolates formed concentration-controlled morphologies. We found two types of monomeric packing and one dimeric type with two trinuclear gold pyrazolates next to each other on the surface. For an octadecyl functionalized derivative all studied concentrations resulted in a dimeric morphology. However, different concentrations led to different transient states during the layer evolution. At low concentrations, a transient monomeric state was present with the alkyl chains in a gauche-conformation that subsequently converted to a more optimized anti-conformation. At higher concentrations a less stable "line"

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“…It is worth noting that the delicate balance between the hydrogen bond and van der Waals interactions plays an important role in controlling self-assembly polymorphism. − Dickerson et al studied polymorphic phenomena by regulating the chain length of isophthalic acid; namely, the self-assembly structure is controlled by the ratio of the two interactions . Although the chain length effects on melting point have been investigated in end-substituted n -alkane homologous series by single-crystal XRD, studies by combining the 2D self-assembly with crystal structure to analyze the relationship between the chain length of alkoxy-substituted conjugated compounds and melting points are relatively scarce. − Hence, it is vital to rethink the chain length effects on improving the properties of functional molecules.…”

Section: Introductionmentioning

confidence: 99%

Systematical Investigation of Chain Length Effect on the Melting Point of a Series of Bifunctional Anthraquinone Derivatives via X-ray Diffraction and Scanning Tunneling Microscopy

Wang

Dong

et al. 2019

J. Phys. Chem. C

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Introducing a continuously changing alkyl chain is effective to modify the conjugated molecule, which is widely used in studying the diversity of two-dimensional (2D) self-assembly and the performance of three-dimensional (3D) bulk materials. In this study, a series of bifunctional anthraquinone derivatives (A-OC n , n = 3−18) are synthesized to investigate the interrelation between the chain length and the melting point by differential scanning calorimetry (DSC). It is observed that the A-OC n (n = 1 and 4) crystallizes in monoclinic and the A-OC n (n = 3, 5, 6) crystallizes in triclinic by single-crystal X-ray diffraction (XRD). With the help of scanning tunneling microscopy (STM), the A-OC n (n = 7−18) is found to exhibit an odd−even alternation in their self-assembled structures. The theoretical calculations for crystal structures and the packing density analyses for selfassembly indicate that the hydrogen bond strength gradually reduces with the increase of the chain length, while the van der Waals interaction is opposite. Namely, the hydrogen bonds and the van der Waals interactions coregulate the variation of melting points. In general, this work provides an understanding at the molecular level on how alkyl chain length regulates the melting point, and we believe that it will have implications for the optimization of future organic materials.

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Adsorption of Aldehydes on a Graphite Substrate: Combined Thermodynamic Study of C6−C13 Homologues with a Structural and Dynamical Study of Dodecanal

Cited by 22 publications

References 54 publications

Manifestations of Non‐Planar Adsorption Geometries of Lead Pyrenocyanine at the Liquid‐Solid Interface

Manifestations of Non‐Planar Adsorption Geometries of Lead Pyrenocyanine at the Liquid‐Solid Interface

STM Study of Gold(I) Pyrazolates: Distinct Morphologies, Layer Evolution, and Cooperative Dynamics

Systematical Investigation of Chain Length Effect on the Melting Point of a Series of Bifunctional Anthraquinone Derivatives via X-ray Diffraction and Scanning Tunneling Microscopy

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