Two-Dimensional Polymerization and Reaction at the Solid/Liquid Interface: Scanning Tunneling Microscopy Study

Xie, Rusong; Song, Yonghai; Wan, Lingli; Yuan, Huizhen; Li, Pengcheng; Xiao, Xianping; Liu, Li; Ye, Shuhong; Lei, Shengbin; Wang, Li

doi:10.2116/analsci.27.129

Cited by 18 publications

(6 citation statements)

References 125 publications

(116 reference statements)

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“…This approach allows for the nanopatterning of surfaces (Figure ). The STM tip can be used to initiate polymerization reactions on solid surfaces as well . For instance, it has been shown that chain polymerizations of the topmost surface layers from substituted diacetylene multilayer films deposited from phenyloctane solutions onto graphite substrates can be initiated by applying a pulsed voltage between the STM tip and the substrate. , In a more detailed study on the STM-tip-induced chain polymerization of 10,12-tricosadiynoic acid in a self-organized monolayer at the interface between a solution of the monomer and a highly oriented pyrolytic graphite, it was shown that oligomers could be produced by applying a short voltage pulse between the STM tip and the sample, with a probability that depends on the length of the applied pulse .…”

Section: Microscopies B Scanningmentioning

confidence: 99%

Probing Liquid/Solid Interfaces at the Molecular Level

2012

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Section: Microscopies B Scanningmentioning

confidence: 99%

Probing Liquid/Solid Interfaces at the Molecular Level

2012

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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%

“…Ordered self-assembled 2D nanostructures are typically observed when the mobility of single molecules is sufficiently high to allow them to diffuse and achieve a configuration desirable for attractive, stabilizing intermolecular interactions. ,, SAMNs are supramolecular systems stabilized by noncovalent bonds, − which permit self-healing of defects that consequently leads to long-range order. ,,, 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, and fundamental considerations, considering that self-assembly phenomena observed in living systems occur in aqueous environments. ,,,− …”

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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“…In addition, owing to the reversible nature of the employed condensation reactions, the resulting covalent networks only exhibit limited chemical stability . Other approaches under ambient conditions encompass electrochemical epitaxial polymerization as well as light and local probe-induced polymerization. ,, Yet, these approaches remain restricted to specifically designed model systems. The development of a more general and flexible approach to the on-surface formation of more robust and functional 1D and 2D polymers motivates the transfer of the Ullmann-type reaction discussed above from UHV to a liquid environment.…”

mentioning

confidence: 99%

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

Eder

Smith²,

Cebula³

et al. 2013

ACS Nano

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The polymerization of 1,3,5-tri(4-iodophenyl)benzene (TIPB) on Au(111) through covalent aryl-aryl coupling is accomplished using a solution-based approach and investigated by scanning tunneling microscopy. Drop-casting of the TIPB monomer onto Au(111) at room temperature results in poorly ordered noncovalent arrangements of molecules and partial dehalogenation. However, drop-casting on a preheated Au(111) substrate yields various topologically distinct covalent aggregates and networks. Interestingly, some of these covalent nanostructures do not adsorb directly on the Au(111) surface, but are loosely bound to a disordered layer of a mixture of chemisorbed iodine and molecules, a conclusion that is drawn from STM data and supported by X-ray photoelectron spectroscopy. We argue that the gold surface becomes covered by a strongly chemisorbed iodine monolayer which eventually inhibits further polymerization.

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Two-Dimensional Polymerization and Reaction at the Solid/Liquid Interface: Scanning Tunneling Microscopy Study

Cited by 18 publications

References 125 publications

Probing Liquid/Solid Interfaces at the Molecular Level

Probing Liquid/Solid Interfaces at the Molecular Level

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

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

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