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

Silly, Fabien

doi:10.1021/jp300678m

Cited by 58 publications

(69 citation statements)

References 26 publications

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“…For example, double hydrogen bonds (O-H•••O) are expected to appear between neighboring molecules possessing carboxylic groups. This strategy has been successfully used to stabilize the formation of porous and compact nanoarchitectures in a highly predictable fashion [35][36][37][38][39][40][41] . However, "push-pull" dyes usually have a complex structure with low symmetry.…”

Section: Introductionmentioning

confidence: 99%

Molecular trapping in two-dimensional chiral organic Kagomé nanoarchitectures composed of Baravelle spiral triangle enantiomers

et al. 2020

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The supramolecular self-assembly of a push-pull dye is investigated using scanning tunneling microscopy (STM) at the liquid-solid interface. The molecule has an indandione head, a bithiophene backbone and a triphenylamine-bithiophene moiety functionalized with two carboxylic acid groups as a tail. The STM images show that the molecules adopt an "L" shape on the surface and form chiral Baravelle spiral triangular trimers at low solution concentrations. The assembly of these triangular chiral trimers on the graphite surface results in the formation of two types of chiral Kagomé nanoarchitectures. The Kagomé-α structure is composed of only one trimer enantiomer, whereas the Kagomé-β structure results from the arrangement of two trimer enantiomers in a 1:1 ratio. These Kagomé lattices are stabilized by intermolecular O-H•••O hydrogen bonds between carboxylic acid groups. These observations reveal that the complex structure of the push-pull dye molecule leads to the formation of sophisticated two-dimensional chiral Kagomé nanoarchitectures. The subsequent deposition of coronene molecules leads to the disappearance of the Kagomé-β structure, whereas the Kagomé-α structure acts as the host template to trap the coronene molecules.

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Section: Introductionmentioning

confidence: 99%

Molecular trapping in two-dimensional chiral organic Kagomé nanoarchitectures composed of Baravelle spiral triangle enantiomers

et al. 2020

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“…[36][37][38] Like for other molecular assemblies at surfaces, the balance between molecule-substrate and intermolecular interactions is a central aspect in the design of carboxylic acid based structures. 2,9,36,[39][40][41][42][43][44][45][46][47][48] At the liquid/solid interface enthalpic and entropic contributions from the solvent also exert decisive influence on structures 20,40,[49][50][51][52] and the electrochemical potential represents an additional control parameter at electrified interfaces. [53][54][55][56][57][58] For molecules like ArCAs the balance involves a number of mutually dependent factors comprising interactions of the πsystems, both intermolecular and with the substrate, hydrogen bonding of the COOH groups, and conformational degrees of freedom.…”

Section: Introductionmentioning

confidence: 99%

Self-assembly of 1,3,5-benzenetribenzoic acid on Ag and Cu at the liquid/solid interface

Aitchison

Morena

et al. 2018

Phys. Chem. Chem. Phys.

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Assembly of 1,3,5-benzenetribenzoic acid (H3BTB) from solution on Au substrates modified by underpotential deposited Ag and Cu layers was studied by near edge X-ray absorption fine structure spectroscopy, X-ray photoelectron spectroscopy and scanning tunneling microscopy. Adsorption of H3BTB on Cu resulted in disordered layers with sporadic occurrence of ordered molecular aggregates. In contrast, highly ordered layers were obtained on Ag which exhibit a pronounced row structure and involve a monopodal bidentate adsorption geometry of the molecules through carboxylate coordinating bonding. The row structure arises from π-stacking of the molecules and is accompanied by hydrogen bonding interactions between the COOH groups of adjacent rows. As a consequence of the geometry of the H3BTB molecule and the dominance of intermolecular over molecule-substrate interactions, the SAM forms an open structure featuring a grooved surface and nanotunnels.

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“…37 1,3,5-Benzenetribenzoic acid (BTB), which has a larger core than TMA, stabilizes into both porous chicken-wire meshes bounded by cyclic O−H···O dimers and more densely packed phases that comprise weaker cyclic O− H···O trimers, trading off the stronger H bonds for increased molecular packing. 38,39 Morrison et al studied the effects of changing the bonding geometry of benzenetribenzoic acids by varying the number and location of carboxylic acids, revealing a remarkable diversity of structures in the corresponding 2D layers. 40 The even larger 1,3,5-tris[4′-carboxy(1,1′-biphenyl-4-yl)]benzene (TCBPB) forms a variation on the chicken-wire structure, where the molecular density on the surface is increased through the offset of molecules and the incorporation of weak C−H···O bonds instead of the stronger O−H···O bonds associated with the unperturbed chicken-wire structure.…”

Section: ■ Introductionmentioning

confidence: 99%

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

Cited by 58 publications

References 26 publications

Molecular trapping in two-dimensional chiral organic Kagomé nanoarchitectures composed of Baravelle spiral triangle enantiomers

Molecular trapping in two-dimensional chiral organic Kagomé nanoarchitectures composed of Baravelle spiral triangle enantiomers

Self-assembly of 1,3,5-benzenetribenzoic acid on Ag and Cu at the liquid/solid interface

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

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