Robust and Open Tailored Supramolecular Networks Controlled by the Template Effect of a Silicon Surface

Baris, Bulent; Luzet, Vincent; Duverger, Eric; Sonnet, Philippe; Palmino, Frank; Cherioux, Frédéric

doi:10.1002/anie.201100332

Cited by 85 publications

(97 citation statements)

References 36 publications

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“…Despite their relatively weak nature, the molecule-substrate interactions have a strong bearing on the adsorption of molecules [36][37][38][39][40][41]. Detailed experimental and theoretical studies have revealed that the tendency of molecules in a two-dimensional monolayer to comply with the registry of the substrate lattice can result in significant changes in intermolecular interactions when compared with their self-assembly in three-dimensional crystals [36].…”

Section: Role Of the Substrate And The Mediummentioning

confidence: 99%

Principles of molecular assemblies leading to molecular nanostructures

Mali

Feyter

2013

Phil. Trans. R. Soc. A.

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Self-assembled physisorbed monolayers consist of regular two-dimensional arrays of molecules. Two-dimensional self-assembly of organic and metal–organic building blocks is a widely used strategy for nanoscale functionalization of surfaces. These supramolecular nanostructures are typically sustained by weak non-covalent forces such as van der Waals, electrostatic, metal–ligand, dipole–dipole and hydrogen bonding interactions. A wide variety of structurally very diverse monolayers have been fabricated under ambient conditions at the liquid–solid and air–solid interface or under ultra-high-vacuum (UHV) conditions at the UHV–solid interface. The outcome of the molecular self-assembly process depends on a variety of factors such as the nature of functional groups present on assembling molecules, the type of solvent, the temperature at which the molecules assemble and the concentration of the building blocks. The objective of this review is to provide a brief account of the progress in understanding various parameters affecting two-dimensional molecular self-assembly through illustration of some key examples from contemporary literature.

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Section: Role Of the Substrate And The Mediummentioning

confidence: 99%

Principles of molecular assemblies leading to molecular nanostructures

Mali

Feyter

2013

Phil. Trans. R. Soc. A.

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“…10 Single 11,12 and multicomponent 1,[13][14][15][16] self-assembled porous nanoarchitectures can be achieved through hydrogen bonding. Building blocks based on molecule having carboxyl groups (COOH) are especially interesting because these groups can form 2 H-Bonds (O-H· · · O).…”

Section: Strong Intermolecular Interactions Are Required To Stabilizementioning

confidence: 99%

Two-Dimensional 1,3,5-Tris(4-carboxyphenyl)benzene Self-Assembly at the 1-Phenyloctane/Graphite Interface Revisited

Silly

2012

J. Phys. Chem. C

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This document is the unedited author's version of a Submitted Work that was subsequently accepted for publication in Journal of Physical Chemistry C, copyright c American Chemical Society after peer review. To access the final edited and published work see http://pubs.rsc.org/en/journals/journalissues/tc. Two-dimensional (2D) self-assembly of star-shaped 1,3,5-Tris(4-carboxyphenyl)benzene molecules is investigated. Scanning tunneling microscopy reveals that this molecule can form three hydrogen-bonded networks at the 1-phenyloctane/graphite interface. One of these structures is close-packed and the two other ones are porous structures, with hexagonal and rectangular cavities. The network with rectangular cavities appears to be the most stable structure.2

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“…7−11 In twodimensional (2D) self-assembled molecular networks (SAMNs) the substrate serves as physical support but can also play an important role in driving formation of a specific pattern. As such, the template effect can be exploited to reinforce or work against 12 the inherent molecular symmetries. Ordered self-assembled 2D nanostructures are typically observed when the mobility of single molecules is sufficiently high to allow them to diffuse and achieve a configuration desirable for attractive, stabilizing intermolecular interactions.…”

Section: ■ Introductionmentioning

confidence: 99%

Substrate, Molecular Structure, and Solvent Effects in 2D Self-Assembly via Hydrogen and Halogen Bonding

et al. 2014

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Recently, halogen···halogen interactions have been demonstrated to stabilize two-dimensional supramolecular assemblies at the liquid−solid interface. Here we study the effect of changing the halogen, and report on the 2D supramolecular structures obtained by the adsorption of 2,4,6-tris(4-bromophenyl)-1,3,5-triazine (TBPT) and 2,4,6-tris(4-iodophenyl)-1,3,5-triazine (TIPT) on both highly oriented pyrolytic graphite and the (111) facet of a gold single crystal. These molecular systems were investigated by combining room-temperature scanning tunneling microscopy in ambient conditions with density functional theory, and are compared to results reported in the literature for the similar molecules 1,3,5-tri(4-bromophenyl)benzene (TBPB) and 1,3,5-tri(4-iodophenyl)benzene (TIPB). We find that the substrate exerts a much stronger effect than the nature of the halogen atoms in the molecular building blocks. Our results indicate that the triazine core, which renders TBPT and TIPT stiff and planar, leads to stronger adsorption energies and hence structures that are different from those found for TBPB and TIPB. On the reconstructed Au(111) surface we find that the TBPT network is sensitive to the fcc-and hcp-stacked regions, indicating a significant substrate effect. This makes TBPT the first molecule reported to form a continuous monolayer at room temperature in which molecular packing is altered on the differently reconstructed regions of the Au(111) surface. Solvent-dependent polymorphs with solvent coadsorption were observed for TBPT on HOPG. This is the first example of a multicomponent self-assembled molecular networks involving the rare cyclic, hydrogen-bonded hexamer of carboxylic groups, R 6 6 (24) synthon.

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Robust and Open Tailored Supramolecular Networks Controlled by the Template Effect of a Silicon Surface

Abstract: International audienc

Cited by 85 publications

References 36 publications

Principles of molecular assemblies leading to molecular nanostructures

Principles of molecular assemblies leading to molecular nanostructures

Two-Dimensional 1,3,5-Tris(4-carboxyphenyl)benzene Self-Assembly at the 1-Phenyloctane/Graphite Interface Revisited

Substrate, Molecular Structure, and Solvent Effects in 2D Self-Assembly via Hydrogen and Halogen Bonding

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