Solution Preparation of Two-Dimensional Covalently Linked Networks by Polymerization of 1,3,5-Tri(4-iodophenyl)benzene on Au(111)

Eder, Georg; Smith, Emily F.; Cebula, Izabela; Heckl, Wolfgang M.; Beton, Peter H.; Lackinger, Markus

doi:10.1021/nn400337v

Cited by 53 publications

(63 citation statements)

References 37 publications

(67 reference statements)

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“…The carbon-iodine bond within an organic molecule is known to dissociate upon adsorption on Au, Ag, and Cu surfaces at room temperature as has been shown for various molecules. 15,[36][37][38] This leads in general to a second reaction step, the intermolecular Ullmann carbon-carbon coupling. 15,16,22,36,[39][40][41][42][43][44][45] Here, our initial aim was to utilize an on-surface chemical reaction to produce covalently bonded linear polymers.…”

Section: Resultsmentioning

confidence: 99%

Manipulating the Conformation of Single Organometallic Chains on Au(111)

et al. 2013

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The conformations of organometallic polymers formed via the bottom-up assembly of monomer units on a metal surface are investigated, and the relationship between the adsorption geometry of the individual monomer units, the conformational structure of the chain, and the overall shape of the polymer is explored. Iodine-functionalized monomer units deposited onto a Au (111) substrate are found to form linear chain structures, where each monomer is linked to its neighbors via an Au adatom. Lateral manipulation of the linear chains using a scanning tunneling microscope allows the structure of the chain to be converted from a linear geometry to a curved one, and it is shown that a transformation of the overall shape of the chain is coupled to a conformational re-arrangement of the chain structure as well as a change in the adsorption geometry of the monomer units within the chain. The observed conformational structure of the curved chain is well ordered and distinct from that of the linear chains. The structures of both the linear and curved chains are investigated by a combination of scanning tunneling microscopy measurements and theoretical calculations.

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Section: Resultsmentioning

confidence: 99%

Manipulating the Conformation of Single Organometallic Chains on Au(111)

et al. 2013

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“…The packing differs from that reported in the literature for similar molecules TIPB and TBPB on HOPG. 41,46,49 This is attributed to stronger molecule···substrate interactions due to the presence of the triazine core, which makes TIPT and TBPT stiffer and planar precursors. Varying the solvents revealed that TBPT can form a bicomponent polymorph involving a hexameric R 6 6 (24) hydrogen-bonded arrangement of the solvent (heptanoic acid) molecules.…”

Section: ■ Conclusion and Perspectivesmentioning

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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“…Eder et al showed that increasing molecular concentration can lead to the formation of a nonorganized second monolayer of 1,3,5-tris(4-iodophenyl)benzene molecules on Au(111). 53 Gatti et al observed that solvent molecules can sometimes interact with molecules without an alkyl chain and form a 2D bicomponent structure on Au(111). 54 In this paper the concentration-dependent self-assembly of 1,3,5-tris(4-iodophenyl)benzene molecules at the 1-phenyloctane/graphite interface is investigated.…”

Section: ■ Introductionmentioning

confidence: 99%

Concentration-Dependent Two-Dimensional Halogen-Bonded Self-Assembly of 1,3,5-Tris(4-iodophenyl)benzene Molecules at the Solid–Liquid Interface

Silly

2017

J. Phys. Chem. C

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The concentration-dependent self-assembly of star-shaped 1,3,5-tris(4-iodophenyl)benzene at the 1-phenyloctane/graphite interface is investigated using scanning tunneling microscopy. The molecules self-assemble into a hexagonal porous halogen-bonded nanoarchitecture at low concentration. This structure is stabilized by X3 synthons. The molecules are oriented along the same direction in this arrangement. At higher concentration two molecular orientations are observed. The molecules then form a porous parallelogram halogen-bonded structure stabilized by X2 synthons. The density of molecular packing is thus higher at high solution concentration. High solution concentration also leads to the appearance of domain boundary in the parallelogram structure. Iodine bonds appear to be a promising alternative to hydrogen bonds to engineer tunable organic porous structures on flat surfaces.

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Solution Preparation of Two-Dimensional Covalently Linked Networks by Polymerization of 1,3,5-Tri(4-iodophenyl)benzene on Au(111)

Cited by 53 publications

References 37 publications

Manipulating the Conformation of Single Organometallic Chains on Au(111)

Manipulating the Conformation of Single Organometallic Chains on Au(111)

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

Concentration-Dependent Two-Dimensional Halogen-Bonded Self-Assembly of 1,3,5-Tris(4-iodophenyl)benzene Molecules at the Solid–Liquid Interface

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