Transformations of Molecular Frameworks by Host–Guest Response: Novel Routes toward Two-Dimensional Self-Assembly at the Solid–Liquid Interface

Cárdenas, Luis; Lipton‐Duffin, Josh; Rosei, Federico

doi:10.1143/jjap.50.08la02

Cited by 10 publications

(3 citation statements)

References 61 publications

(86 reference statements)

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“…This type of guest-induced transformation has been observed previously in self-assembled structures at the solution/solid interface 59,60 and commonly occurs in densely packed structures that cannot natively accommodate guest molecules. This is the case for the offset zigzag structure, which does not offer sufficient access to the underlying HOPG for coronene to adsorb in a flat conformation.…”

Section: ■ Discussionsupporting

confidence: 55%

Two-Dimensional Self-Assembly of a Symmetry-Reduced Tricarboxylic Acid

MacLeod

Chaouch

Perepichka³

et al. 2013

Langmuir

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ABSTRACT:Investigations of the self-assembly of simple molecules at the solution/solid interface can provide useful insight into the general principles governing supramolecular chemistry in two dimensions. Here, we report on the assembly of 3,4′,5-biphenyl tricarboxylic acid (H 3 BHTC), a small hydrogen bonding unit related to the much-studied 1,3,5-benzenetricarboxylic acid (trimesic acid, TMA), which we investigate using scanning tunneling microscopy (STM) and density functional theory (DFT) calculations. STM images show that H 3 BHTC assembles by itself into an offset zigzag chain structure that maximizes the surface molecular density in favor of maximizing the number density of strong cyclic hydrogen bonds between the carboxylic groups. The offset geometry creates "sticky" pores that promote solvent coadsorption. Adding coronene to the molecular solution produces a transformation to a high-symmetry host−guest lattice stabilized by a dimeric/trimeric hydrogen bonding motif similar to the TMA flower structure. Finally, we show that the H 3 BHTC lattice firmly immobilizes the guest coronene molecules, allowing for high-resolution imaging of the coronene structure.

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Section: ■ Discussionsupporting

confidence: 55%

Two-Dimensional Self-Assembly of a Symmetry-Reduced Tricarboxylic Acid

MacLeod

Chaouch

Perepichka³

et al. 2013

Langmuir

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“…1,9,13 SAMNs are supramolecular systems stabilized by noncovalent bonds, 14−16 which permit self-healing of defects that consequently leads to long-range order. 2,5,17,18 The study of self-assembly at the liquid−solid interface is interesting both for pragmatic experimental reasons, since it allows for easy and low-cost fabrication and characterization methods relative to ultrahigh vacuum (UHV) techniques, 19 and fundamental considerations, considering that self-assembly phenomena observed in living systems occur in aqueous environments. 1,2,14,20−22 SAMNs can be stabilized by a number of weak forces, for example, van der Waals (vdW), 23−25 π−π stacking, 12,26 or hydrogen bonding.…”

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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“…Physisorbed monolayers at the solid/liquid interface have been extensively studied for revealing the supramolecular interactions in the formation of self-assembled monolayers [29][30][31][32][33][34]. Several intermolecular interactions take place at the solid/ liquid interface that should be taken into account for the controlled molecular organization in two dimensions, namely molecule-molecule, molecule-substrate, and solvent-molecule interactions (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Two-dimensional molecular networks at the solid/liquid interface and the role of alkyl chains in their building blocks

Liu,

Norikane,

Kikkawa

2023

Beilstein J. Nanotechnol.

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Nanoarchitectonics has attracted increasing attention owing to its potential applications in nanomachines, nanoelectronics, catalysis, and nanopatterning, which can contribute to overcoming global problems related to energy and environment, among others. However, the fabrication of ordered nanoarchitectures remains a challenge, even in two dimensions. Therefore, a deeper understanding of the self-assembly processes and substantial factors for building ordered structures is critical for tailoring flexible and desirable nanoarchitectures. Scanning tunneling microscopy is a powerful tool for revealing the molecular conformations, arrangements, and orientations of two-dimensional (2D) networks on surfaces. The fabrication of 2D assemblies involves non-covalent interactions that play a significant role in the molecular arrangement and orientation. Among the non-covalent interactions, dispersion interactions that derive from alkyl chain units are believed to be weak. However, alkyl chains play an important role in the adsorption onto substrates, as well as in the in-plane intermolecular interactions. In this review, we focus on the role of alkyl chains in the formation of ordered 2D assemblies at the solid/liquid interface. The alkyl chain effects on the 2D assemblies are introduced together with examples documented in the past decades.

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Transformations of Molecular Frameworks by Host–Guest Response: Novel Routes toward Two-Dimensional Self-Assembly at the Solid–Liquid Interface

Cited by 10 publications

References 61 publications

Two-Dimensional Self-Assembly of a Symmetry-Reduced Tricarboxylic Acid

Two-Dimensional Self-Assembly of a Symmetry-Reduced Tricarboxylic Acid

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

Two-dimensional molecular networks at the solid/liquid interface and the role of alkyl chains in their building blocks

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