Tailored Molecular Design for Supramolecular Network Engineering on a Silicon Surface

Makoudi, Younes; Baris, Bulent; Jeannoutot, Judicaël; Palmino, Frank; Grandidier, B.; Cherioux, Frédéric

doi:10.1002/cphc.201200822

Cited by 18 publications

(38 citation statements)

References 45 publications

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“…This qualitative behavior has already been reported for the similar molecule TIPB. 48 The protrusions associated with the iodine atoms do not have the 3-fold symmetry expected for TIPT molecules. We ascribe this to an electronic effect.…”

Section: ■ Results and Discussionmentioning

confidence: 98%

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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Section: ■ Results and Discussionmentioning

confidence: 98%

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

et al. 2014

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“…Our work in this domain illustrates well the effect of temperature in self-assembly formation [22][23][24]. Although molecular deposition Reprinted with permission from [19] was performed at room temperature, this thermal energy was sufficient for molecules to overcome diffusion barriers and then form different self-assemblies.…”

Section: Heatmentioning

confidence: 90%

“…Recently, we have demonstrated that the molecule-surface interactions can be controlled by using the Si(111)-B-(√3 × √3)-R30°surface, noted Si(111)-B. The silicon adatoms dangling bonds are depopulated because of the presence of a boron atom underneath each silicon adatom, leading to a weak π-conjugated moleculesurface interaction [22,24,[50][51][52]. In all these cases, molecule-surface interaction is weak enough to achieve the formation of large-scale supramolecular networks.…”

Section: Adsorption Of Bistable Azobenzene Molecules On Semiconductorsmentioning

confidence: 99%

Single Molecular Machines on Semiconductor Surfaces

Makoudi

Palmino

Cherioux

2015

Single Molecular Machines and Motors

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The development of nanomachines is a key challenge for the future electronics, energy conversion, biology, and medicine. Semiconductor surfaces have been one of the basic elements of many technologies for 40 years. However, despite their promising interest, semiconductor-based nanomachines are almost unstudied. In this work, a panel of single nanomachines-based semiconductor surfaces is described. The role of molecule-surface interaction for the development of nanomachines is highlighted.

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“…Supramolecular networks on a doped boron silicon surface under ultra high vacuum (UHV) have been recently obtained (Makoudi et al, 2013). The used molecule contains different end-groups, bearing either bromine, iodine or hydrogen atoms denoted 1,3,5-tri(4 -bromophenyl)benzene (TBB), 1,3,5-tri(4-iodophenyl)benzene (TIB) and 1,3,5-triphenyl-benzene (THB).…”

Section: Introductionmentioning

confidence: 99%

Theoretical study of intermolecular interactions in nanoporous networks on boron doped silicon surface

Boukari

Duverger

Hanf

et al. 2014

Chemical Physics Letters

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Tailored Molecular Design for Supramolecular Network Engineering on a Silicon Surface

Cited by 18 publications

References 45 publications

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

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

Single Molecular Machines on Semiconductor Surfaces

Theoretical study of intermolecular interactions in nanoporous networks on boron doped silicon surface

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