Structural investigation of caffeine monolayers on Au(111)

Schulte, Malte G. H.; Jeindl, Andreas; Baltaci, Ismail; Roese, Peter; Schmitz, Marie; Berges, U.; Hofmann, Oliver; Westphal, C.

doi:10.1103/physrevb.101.245414

Cited by 3 publications

(3 citation statements)

References 37 publications

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“…The herringbone reconstruction is a feature of the Au(111) surface that arises due to the lack of coordination of the surface layer compared to the bulk layers, resulting in a contraction of Au atoms on the surface layer which is resolved in our images (Figures c and ) as “herringbone” rows of periodic change in contrast. Perturbations in the periodicity of the herringbone reconstruction are a good indicator of molecule–surface interaction strength. , Caffeine, a structurally similar molecule to the molecules in the present study, was shown to have weak interactions with the Au(111) surface as demonstrated by no structural changes to the herringbone reconstruction . Here, we suggest that 5-methylisatin does not strongly interact with the underlying gold surface, given no structural change to the herringbone reconstruction.…”

Section: Resultssupporting

confidence: 53%

“…39,40 Caffeine, a structurally similar molecule to the molecules in the present study, was shown to have weak interactions with the Au(111) surface as demonstrated by no structural changes to the herringbone reconstruction. 41 Here, we suggest that 5methylisatin does not strongly interact with the underlying gold surface, given no structural change to the herringbone reconstruction. However, the observation that the rows of 5methylisatin pentamers pack perpendicular to the herringbone suggests that the underlying gold surface may influence orientational packing of the monolayer structure.…”

Section: ■ Methodsmentioning

confidence: 69%

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Methylisatin Structural Isomers Have Different Kinetic Pathways to Self-Assembly

et al. 2020

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Monolayers of methylisatin structural isomers are prepared on the Au(111) surface and imaged using scanning tunneling microscopy in ultrahigh vacuum. Monolayer preparation via solution deposition results in different monolayer structures for these two isomers. 5-Methylisatin forms rectangular hexamer clusters that are closely packed, while 6-methylisatin forms cyclic pentamers, dimers, and a close-packed phase. Monolayer preparation via vapor deposition results in the formation of cyclic pentamers for both 5- and 6-methylisatin. These results are compared to isatin monolayers, which also form cyclic pentamers upon both solution and vapor deposition. DFT binding energy calculations corroborate a stable pentamer, as there is a calculated binding energy well for 5-molecule clusters for isatin, 5-methylisatin, 6-methylisatin. The formation of the unusual 5-methylisatin hexamer structure is likely due to nonequilibrium adsorption kinetics present in the solution (pulse) deposition preparation technique.

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Section: Resultssupporting

confidence: 53%

Section: ■ Methodsmentioning

confidence: 69%

Methylisatin Structural Isomers Have Different Kinetic Pathways to Self-Assembly

et al. 2020

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“…Theophylline is an isomer of theobromine with a different methyl arrangement. Also, caffeine on Au(111) shows prochirality 16 which differs from theobromine in an additional methyl-group replacing one hydrogen atom bonded to nitrogen. Focusing on surfaceinduced chirality, we utilized room-temperature STM and lowenergy electron diffraction (LEED) to study the theobromine self-assembly on Au(111).…”

Section: ■ Introductionmentioning

confidence: 99%

Structural Analysis of Theobromine Monolayers on Weakly Interacting Surfaces

2020

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Theobromine molecules and related compounds such as caffeine and theophylline are of importance for pharmacology, toxicology, and biochemistry. In this field, it is fundamental to study the emergence of chirality. Chirality can emerge because of surface adsorption. Therefore, it is necessary to study the chiral adsorption of theobromine on the surface. Here, we present the first experimental comparative study of theobromine monolayers on Au(111) and on few-layer graphene on SiC(0001). The self-assembly of theobromine is characterized utilizing scanning tunneling microscopy and low-energy electron diffraction. Additionally, simulations with LEEDpat are performed and compared with the experimental data. We found that the adsorbate unit cell is rectangular and consists of four molecules. Theobromine shows geometrically similar unit cells on both substrates. On Au(111), the molecules are prochiral, with two enantiomers in a zig-zag structure, which is explained by glide reflections.

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Caffeine as an energy storage material for next-generation lithium batteries

Lee

Park

et al. 2023

Energy Storage Materials

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Structural investigation of caffeine monolayers on Au(111)

Cited by 3 publications

References 37 publications

Methylisatin Structural Isomers Have Different Kinetic Pathways to Self-Assembly

Methylisatin Structural Isomers Have Different Kinetic Pathways to Self-Assembly

Structural Analysis of Theobromine Monolayers on Weakly Interacting Surfaces

Caffeine as an energy storage material for next-generation lithium batteries

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