Two-Dimensional Self-Assembled Structures of Melamine and Melem at the Aqueous Solution−Au(111) Interface

Uemura, Shinobu; Aono, Masashi; Komatsu, Toshimitsu; Kunitake, Masashi

doi:10.1021/la103948n

Cited by 65 publications

(57 citation statements)

References 50 publications

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“…As typical examples of self-assembled structures including "order-order" phase transitions, Figure 2 shows highly ordered adlayer structures of two triangular building block molecules, trimesic acid (TMA), [32] and 2,5,8-triamino-tri-s-triazine (melem) [33] with their "order-order" phase transitions.…”

Section: -1 2-d Supramolecular Arrangements and Their Scanning Tunnmentioning

confidence: 99%

Self-assembled π-conjugated macromolecular architectures — A soft solution process based on Schiff base coupling

Kunitake

Higuchi

Tanoue

et al. 2014

Current Opinion in Colloid & Interface Science

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Two-dimensional supramolecular covalent macromolecular architectures were visualized directly by in-situ scanning tunneling microcopy and colorful -conjugated nanofilms with unique mesostructures formed spontaneously on hydrophobic substrates from aqueous solutions in the presence of simple aromatic building block molecules under ambient conditions. We thus report the results of surface-mediated polycondensation and chemical liquid deposition. The Schiff base coupling reaction applied for this soft solution process is a dynamic reversible covalent coupling reaction that can be managed by careful changes in solution conditions based on 'adsorption' and 'polymerization' equilibria. This low-cost and eco-friendly 'bottom-up' method allows great diversity in terms of the design of primary polymeric chemical structures by the selection of building blocks without the need to consider the solubility of the polymer. This paves the way to a true 'bottom-up' assembly of a vast array of solid-supported, designer supramolecular nanoarchitectures with potential use as functional materials for next-generation organic electronics.

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Section: -1 2-d Supramolecular Arrangements and Their Scanning Tunnmentioning

confidence: 99%

Self-assembled π-conjugated macromolecular architectures — A soft solution process based on Schiff base coupling

Kunitake

Higuchi

Tanoue

et al. 2014

Current Opinion in Colloid & Interface Science

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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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“…[21][22][23] These chiral assemblies can be stabilized by hydrogen bonding, but the origin of chirality mostly comes from the initial chirality of the molecules themselves. It is in particular the case of polyaromatic and heterocyclic compounds, 24,25 but also of the so-called bio-molecules like amino acids 26 or nucleic acid building blocks 27 which drive the research in the promising areas of biosensors and biomaterials.…”

Section: Introductionmentioning

confidence: 99%

Two-Dimensional Self-Assembly Monitored by Hydrogen Bonds for Triphenylene-Based Molecules: New Role for Azobenzenes

et al. 2016

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A hybrid disk-like/rod-like molecule comprising central triphenylene core symmetrically substituted with six azobenzene moieties (C-12) has been adsorbed at the 1,2,4trichlorobenzene/Au(111) interface, revealing the potential of azobenzene moieties for the control of 2D chiral networks. The C-12, which due to its complex molecular structure possesses a relatively large number of degrees of freedom, surprisingly forms monolayers of only one kind of structure, namely a hexagonal network of large period, 3.5 nm. By combining Scanning Tunneling Microscopy (STM) and DFT calculations, we evidence that this specific 2D-ordering is due to cooperative weak hydrogen bonds between neighboring azobenzenes and azobenzene-Au(111) interactions. The crystallographic network is hexagonal, but azobenzene-azobenzene pairing, associated with hydrogen bonding renders the network chiral with a chirality spanning all ranges, from the molecular C-12 configuration, the configuration of the azobenzene dimers and the rosette-like azobenzene network, to the C-12 network orientation on Au(111) rotated by ±8° from the main crystallographic direction Au<110>, depending on the handedness of the molecular network. This chiral 2D system thus paves the way for the formation of macroscopic 2D molecular crystals of unique handedness, if additional enantiomeric chiral dopants can be used.

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Two-Dimensional Self-Assembled Structures of Melamine and Melem at the Aqueous Solution−Au(111) Interface

Cited by 65 publications

References 50 publications

Self-assembled π-conjugated macromolecular architectures — A soft solution process based on Schiff base coupling

Self-assembled π-conjugated macromolecular architectures — A soft solution process based on Schiff base coupling

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

Two-Dimensional Self-Assembly Monitored by Hydrogen Bonds for Triphenylene-Based Molecules: New Role for Azobenzenes

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