Self-Assembled Melamine Monolayer on Cu(111)

Lin, Yu-Pu; Ourdjini, Oualid; Giovanelli, Luca; Clair, Sylvain; Faury, Thomas; Ksari, Younal; Themlin, J.‐M.; Porte, L.; Abel, Markus

doi:10.1021/jp401496s

Cited by 53 publications

(79 citation statements)

References 52 publications

(113 reference statements)

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“…The sharp N 1s peak indicates a single chemical species, thereby corroborating the anticipated chemical equivalency of all the nitrogen atoms. The measured binding energy (BE) of 399.8 eV is in accord with NH 2 groups on aromatic moieties, with similar BEs reported for aniline, 1,3‐phenyldiamine, tetraamine, and melamine adsorbed on various metal surfaces. The C 1s XP spectrum shown in Figure b required fitting with two chemically shifted components with BEs of 284.7 and 285.7 eV, which resulted in a peak area ratio of 67:33.…”

Section: Resultsmentioning

confidence: 99%

Competitive Metal Coordination of Hexaaminotriphenylene on Cu(111) by Intrinsic Copper Versus Extrinsic Nickel Adatoms

Lischka

Dong

Wang

et al. 2019

Chemistry A European J

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The interplay between the self‐assembly and surface chemistry of 2,3,6,7,10,11‐hexaaminotriphenylene (HATP) on Cu(111) was complementarily studied by high‐resolution scanning tunneling microscopy (STM) and X‐ray photoelectron spectroscopy (XPS) under ultra‐high vacuum conditions. To shed light on the competitive metal coordination, comparative experiments were carried out on pristine and nickel‐covered Cu(111). Directly after room‐temperature deposition of HATP onto pristine Cu(111), self‐assembled aggregates were observed by STM, and XPS results indicated still protonated amino groups. Annealing up to 200 °C activated the progressive single deprotonation of all amino groups as indicated by chemical shifts of both the N 1s and C 1s core levels in the XP spectra. This enabled the formation of topologically diverse π–d conjugated coordination networks with intrinsic copper adatoms. The basic motif of these networks was a metal–organic trimer, in which three HATP molecules were coordinated by Cu3 clusters, as corroborated by the accompanying density functional theory (DFT) simulations. Additional deposition of more reactive nickel atoms resulted in both chemical and structural changes with deprotonation and formation of bis(diimino)–Ni bonded networks already at room temperature. Even though fused hexagonal metal‐coordinated pores were observed, extended honeycomb networks remained elusive, as tentatively explained by the restricted reversibility of these metal–organic bonds.

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Section: Resultsmentioning

confidence: 99%

Competitive Metal Coordination of Hexaaminotriphenylene on Cu(111) by Intrinsic Copper Versus Extrinsic Nickel Adatoms

Lischka

Dong

Wang

et al. 2019

Chemistry A European J

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“…The energy position differs significantly (1.1 eV lower), from the one observed after Cu coordination of 3deh-DPDI on Cu(111), and is assigned to imino-nitrogen atoms. 79,80 Upon annealing at ~300 °C the N1s peak remains virtually unchanged (~398.1 eV) (Figure 2d). The core level shift between this Co-coordinated imine and th imine N has been calculated to be 0.69 eV, which comp well to the experimental data.…”

Section: Resultsmentioning

confidence: 99%

Controlling the Dimensionality of On-Surface Coordination Polymers via Endo- or Exoligation

et al. 2014

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ABSTRACT:The formation of on-surface coordination polymers is controlled by the interplay of chemical reactivity and structure of the building blocks, as well as by the orientating role of the substrate registry. Beyond the pre-determined patterns of structural assembly, the chemical reactivity of the reactants involved may provide alternative pathways in their aggregation. Organic molecules, which are transformed in a surface reaction, may be subsequently trapped via coordination of homo-or heterometal adatoms, which may also play a role in the molecular transformation itself. The amino-functionalized perylene derivative, 4,9-diaminoperylene-quinone-3,10-diimine (DPDI), undergoes specific levels of dehydrogenation (-1 H 2 or -3 H 2 ) depending on the nature of the present adatoms (Fe, Co, Ni or Cu, respectively). In this way, the molecule is converted to an endo-or an exo-ligand, possessing a concave or convex arrangement of ligating atoms, which is decisive for the formation of either 1D or 2D coordination polymers.

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“…The second process is a ring‐opening polymerization reaction of melamine on Cu(111) as disclosed by Abel and co‐workers . Annealing of the organic compound to 150 °C resulted in the formation of linear chains, and increasing reaction temperature to 300 °C then allowed for creation of a covalent connected two‐dimensional network.…”

Section: Other Chemical Functionalities In On‐surface Reactionsmentioning

confidence: 99%

Covalent‐Bond Formation via On‐Surface Chemistry

Held

Fuchs

Studer

2017

Chemistry A European J

144

134

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In this Review article pioneering work and recent achievements in the emerging research area of on-surface chemistry is discussed. On-surface chemistry, sometimes also called two-dimensional chemistry, shows great potential for bottom-up preparation of defined nanostructures. In contrast to traditional organic synthesis, where reactions are generally conducted in well-defined reaction flasks in solution, on-surface chemistry is performed in the cavity of a scanning probe microscope on a metal crystal under ultrahigh vacuum conditions. The metal first acts as a platform for self-assembly of the organic building blocks and in many cases it also acts as a catalyst for the given chemical transformation. Products and hence success of the reaction are directly analyzed by scanning probe microscopy. This Review provides a general overview of this chemistry highlighting advantages and disadvantages as compared to traditional reaction setups. The second part of the Review then focuses on reactions that have been successfully conducted as on-surface processes. On-surface Ullmann and Glaser couplings are addressed. In addition, cyclodehydrogenation reactions and cycloadditions are discussed and reactions involving the carbonyl functionality are highlighted. Finally, the first examples of sequential on-surface chemistry are considered in which two different functionalities are chemoselectively addressed. The Review gives an overview for experts working in the area but also offers a starting point to non-experts to enter into this exciting new interdisciplinary research field.

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Self-Assembled Melamine Monolayer on Cu(111)

Cited by 53 publications

References 52 publications

Competitive Metal Coordination of Hexaaminotriphenylene on Cu(111) by Intrinsic Copper Versus Extrinsic Nickel Adatoms

Competitive Metal Coordination of Hexaaminotriphenylene on Cu(111) by Intrinsic Copper Versus Extrinsic Nickel Adatoms

Controlling the Dimensionality of On-Surface Coordination Polymers via Endo- or Exoligation

Covalent‐Bond Formation via On‐Surface Chemistry

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