Surface‐Confined Self‐Assembly of Di‐carbonitrile Polyphenyls

Klyatskaya, Svetlana; Klappenberger, Florian; Schlickum, Uta; Kühne, Dirk; Marschall, Matthias; Reichert, Joachim; Decker, Régis; Krenner, Wolfgang; Zoppellaro, Giorgio; Brune, Harald; Barth, Johannes V.; Rüben, Mario

doi:10.1002/adfm.201001437

Cited by 63 publications

(67 citation statements)

References 78 publications

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“…[14][15][16][17] Different molecular patternss uch as 0D clusters, 1D chains and 2D islands can be createdb yc hanging the number of cyano groups and/or their relative position, as was demonstrated for cyanofunctionalized porphyrin and polyphenylene derivatives. [4,14,18] Herein, we report on the self-assembly of the cyanofunctionalized planarized triarylamined erivative 4,4,8,8,12,12-hexamethyl-4H,8H,12H-benzo[1,9]quinolizino[3,4,5,6,7-defg]acridine-2,6,10-tricarbonitrile (1,S cheme1)o nc oinage metal (111) surfaces. Such planarized triarylamines, so-called heterotriangulenes, are at presento fg rowing interest owing to their potential as stable electron-rich building blocksf or optoelectronic organic materials.…”

Section: Introductionmentioning

confidence: 99%

Cyano‐Functionalized Triarylamines on Coinage Metal Surfaces: Interplay of Intermolecular and Molecule–Substrate Interactions

Müller

Moreno-López

Gottardi

et al. 2015

Chemistry A European J

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The self-assembly of cyano-functionalized triarylamine derivatives on Cu(111), Ag(111) and Au(111) was studied by means of scanning tunnelling microscopy, low-energy electron diffraction, X-ray photoelectron spectroscopy and density functional theory calculations. Different bonding motifs, such as antiparallel dipolar coupling, hydrogen bonding and metal coordination, were observed. Whereas on Ag(111) only one hexagonally close-packed pattern stabilized by hydrogen bonding is observed, on Au(111) two different partially porous phases are present at submonolayer coverage, stabilized by dipolar coupling, hydrogen bonding and metal coordination. In contrast to the self-assembly on Ag(111) and Au(111), for which large islands are formed, on Cu(111), only small patches of hexagonally close-packed networks stabilized by metal coordination and areas of disordered molecules are found. The significant variety in the molecular self-assembly of the cyano-functionalized triarylamine derivatives on these coinage metal surfaces is explained by differences in molecular mobility and the subtle interplay between intermolecular and molecule-substrate interactions.

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Section: Introductionmentioning

confidence: 99%

Cyano‐Functionalized Triarylamines on Coinage Metal Surfaces: Interplay of Intermolecular and Molecule–Substrate Interactions

Müller

Moreno-López

Gottardi

et al. 2015

Chemistry A European J

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“…Additionally, cyano groups (CN‐groups) can undergo metal‐ligand interactions resulting in the formation of highly stable structures . In this respect, the self‐assembly of dicarbonitrile polyphenyl derivatives on Ag(111) was extensively studied . For room temperature deposition and coverages below one monolayer, the observed structures are stabilized by hydrogen bonding while the co‐deposition of metal atoms leads to the formation of hexagonal metal‐coordinated porous networks, whose pore size can be steered by the number of phenyl rings per molecule .…”

Section: Introductionmentioning

confidence: 99%

Cyano‐Functionalized Triarylamines on Au(111): Competing Intermolecular versus Molecule/Substrate Interactions

Gottardi

Müller

Moreno-López

et al. 2013

Adv Materials Inter

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The self-assembly of cyano-substituted triarylamine derivatives on Au(111) is studied with scanning tunneling microscopy and density functional theory calculations. Two different phases, each stabilized by at least two different cyano bonding motifs are observed. In the first phase, each molecule is involved in dipolar coupling and hydrogen bonding, while in the second phase, dipolar coupling, hydrogen bonding and metal-ligand interactions are present.Interestingly, the metal-ligand bond is already observed for deposition of the molecules with the sample kept at room temperature leaving the herringbone reconstruction unaffected. We propose that for establishing this bond, the Au atoms are slightly displaced out of the surface to bind to the cyano ligands. Despite the intact herringbone reconstruction, the Au substrate is found to considerably interact with the cyano ligands affecting the conformation and adsorption geometry, as well as leading to correlation effects on the molecular orientation.

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“…[1,2] During self-assembly, adsorbates diffuse and adjust their orientation to form regular superstructures. The result is a delicate balance between supramolecular chemistry (dipole-dipole interactions, hydrogen bonding, and van der Waals forces) and molecule-surface interactions.…”

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confidence: 99%

Quantum Influences in the Diffusive Motion of Pyrrole on Cu(111)

et al. 2013

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The adsorption of aromatic molecules on surfaces is of broad interest in the fields of self-assembled networks and selforganized growth. [1,2] During self-assembly, adsorbates diffuse and adjust their orientation to form regular superstructures. The result is a delicate balance between supramolecular chemistry (dipole-dipole interactions, hydrogen bonding, and van der Waals forces) and molecule-surface interactions. These factors determine the structure, energy, site-specificity, and two-dimensional molecular translational and rotational diffusion. [2][3][4][5] Differently substituted polyaromatic rings form key building blocks, [6] defining the structure of chemically functionalized surfaces. It is crucial to understand the motion of single molecular precursors to gain insight into the complex processes underlying self-assembly. Aromatic adsorbates are extended particles of large mass that are assumed to obey classical mechanics for temperatures where self-assembly occurs. We will see, however, that quantum effects can nevertheless play a crucial role in the dynamics of surface diffusion even when the quantized degrees of freedom are not associated directly with translational motion.Here, we study pyrrole, C 4 H 4 NH, an important precursor for many chemically and technologically relevant materials. In recent years, functionalized pyrroles and related molecules have attracted increasing attention as self-assembling adsorbates. [7] Pyrrole has been studied on several metal surfaces, including Pt(111), [8] Pd (111), [9] Rh(111), [10] and Cu(100). [11] Whilst little is known about potential energy landscapes and interactions between molecules, pyrrole is usually found to adsorb in a flat-lying geometry at low coverages, often moving to a tilted geometry at higher coverages.Herein we describe a helium spin-echo (HeSE) and density functional theory (DFT) study of the dynamics of this elementary building block on Cu(111) to investigate interadsorbate interactions, the effect of friction, and the role of quantum modes in a sub-monolayer regime. We will show that the behavior is dominated by the quantum contribution to the total energy of pyrroles vibrational ground state. Surprisingly, the important vibrations are not those associated with motion of the center of mass but are internal modes.The HeSE method is new and uniquely sensitive to atomic scale motion on pico-to nanosecond timescales. [12] Figure 1 illustrates the principle, showing how surface motion occurring over a time difference, t SE , reduces coherent scattering and gives a correlation function that typically decays with time as f(t) = a exp(Àat SE ) + c. [12] The characteristic timescale of the motion is then given by the decay rate, a, which depends on the angle of scattering. Motion, in real space, is deduced by comparing the dependence on scattering angle, expressed as a momentum transfer, DK, with Langevin molecular dynamics (MD) simulations. [13] We have performed experiments at (121-170) K along two crystal directions. The resulting a(DK) depend...

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Surface‐Confined Self‐Assembly of Di‐carbonitrile Polyphenyls

Cited by 63 publications

References 78 publications

Cyano‐Functionalized Triarylamines on Coinage Metal Surfaces: Interplay of Intermolecular and Molecule–Substrate Interactions

Cyano‐Functionalized Triarylamines on Coinage Metal Surfaces: Interplay of Intermolecular and Molecule–Substrate Interactions

Cyano‐Functionalized Triarylamines on Au(111): Competing Intermolecular versus Molecule/Substrate Interactions

Quantum Influences in the Diffusive Motion of Pyrrole on Cu(111)

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