Self-assembly of pyrene derivatives on Au(111): substituent effects on intermolecular interactions

Pham, Tuan Anh; Song, Fei; Nguyen, Manh‐Thuong; Stöhr, Meike

doi:10.1039/c4cc02753a

Cited by 68 publications

(86 citation statements)

References 23 publications

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“…The self‐assembled network formed by the mono‐brominated compound 7 is somewhat similar to that formed by 6 (Figure f, i). Similar to the results described above, the influence of the number of Br substituents on 2D self‐assembly of a pyrene derivative has been reported on Au(111) surface using UHV STM carried out at room temperature …”

Section: Halogen‐halogen Interactions and Halogen‐bonding In Self‐asssupporting

confidence: 78%

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Halogen Bonding in Two‐Dimensional Crystal Engineering

2020

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Halogen bonds, which provide an intermolecular interaction with moderate strength and high directionality, have emerged as a promising tool in the repertoire of non‐covalent interactions. In this review, we provide a survey of the literature where halogen bonding was used for the fabrication of supramolecular networks on solid surfaces. The definitions of, and the distinction between halogen bonding and halogen‐halogen interactions are provided. Self‐assembled networks formed at the solution/solid interface and at the vacuum‐solid interface, stabilized in part by halogen bonding, are discussed. Besides the broad classification based on the interface at which the systems are studied, the systems are categorized further as those sustained by halogen‐halogen and halogen‐heteroatom contacts.

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Section: Halogen‐halogen Interactions and Halogen‐bonding In Self‐asssupporting

confidence: 78%

“…atoms covalently bonded to C atoms) . Similar quadruple nodes based on X 4 synthons have been reported for self‐assembly of brominated pyrenes on Au(111) under UHV conditions …”

Section: Halogen‐halogen Interactions and Halogen‐bonding In Self‐asssupporting

confidence: 75%

Halogen Bonding in Two‐Dimensional Crystal Engineering

2020

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“…The formed triangular binding motif consists of both Br−Br halogen and Br−H hydrogen bonds, which are responsible for the network formation. More information can be found in our recent report on monolayer coverage of the same molecule on Au(111) with room temperature STM measurements …”

Section: Resultsmentioning

confidence: 99%

“…More information can be found in our recent report on monolayer coverage of the same molecule on Au(111)w ith room temperature STM measurements. [49] To initiate ac ovalent coupling reactionb etween the Br 4 Py molecules on Au(111), the sample was annealed at 473 Kf or 15 min and subsequentlyc ooled to 77 Kf or the STM measurements.From the STM image in Figure 6a,t he disappearance of the 2D self-assembled patterns can be inferred. Instead, disordered 2D arrays and clusters were observed.…”

Section: On-surfacep Olymerization Of Br 4 Py On Au(111)mentioning

confidence: 99%

Comparing Ullmann Coupling on Noble Metal Surfaces: On‐Surface Polymerization of 1,3,6,8‐Tetrabromopyrene on Cu(111) and Au(111)

Pham

Song

Nguyen

et al. 2016

Chemistry A European J

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106

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The on-surface polymerization of 1,3,6,8-tetrabromopyrene (Br4 Py) on Cu(111) and Au(111) surfaces under ultrahigh vacuum conditions was investigated by a combination of scanning tunneling microscopy (STM), X-ray photoelectron spectroscopy (XPS) and density functional theory (DFT) calculations. Deposition of Br4 Py on Cu(111) held at 300 K resulted in a spontaneous debromination reaction, generating the formation of a branched coordination polymer network stabilized by C-Cu-C bonds. After annealing at 473 K, the C-Cu-C bonds were converted to covalent C-C bonds, leading to the formation of a covalently linked molecular network of short oligomers. In contrast, highly ordered self-assembled two-dimensional (2D) patterns stabilized by both Br-Br halogen and Br-H hydrogen bonds were observed upon deposition of Br4 Py on Au(111) held at 300 K. Subsequent annealing of the sample at 473 K led to a dissociation of the C-Br bonds and the formation of disordered metal-coordinated molecular networks. Further annealing at 573 K resulted in the formation of covalently linked disordered networks. Importantly, we found that the chosen substrate not only plays an important role as catalyst for the Ullmann reaction, but also influences the formation of different types of intermolecular bonds and thus, determines the final polymer network morphology. DFT calculations further support our experimental findings obtained by STM and XPS and add complementary information on the reaction pathway of Br4 Py on the different substrates.

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“…In addition, the metal substrate not only serves as a support of low dimensional nanostructures, but also decreases the activation energy of dehydrogenation, leading to more participants in the process of coupling after C-H bond being separated [19][20][21][22]. On one hand, metal substrates decrease the relatively large bond dissociation enthalpy to let the action be easily done.…”

Section: Dehydrogenation Reactionmentioning

confidence: 99%

Recent Progress in the Fabrication of Low Dimensional Nanostructures via Surface-Assisted Transforming and Coupling

Liang

Shen

et al. 2017

Journal of Nanomaterials

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Polymerization of functional organics into covalently cross-linked nanostructures via bottom-up approach on solid surfaces has attracted tremendous interest recently, due to its appealing potentials in fabricating novel and artificial low dimensional nanomaterials. While there are various synthetic approaches being proposed and explored, this paper reviews the recent progress of on-surface coupling strategies towards the synthesis of low dimensional nanostructures ranging from 1D nanowire to 2D network and describes their advantages and drawbacks during on-surface process and phase transformations, for example, from molecular self-assembly to on-surface polymerization. Specifically, Ullmann reaction is discussed in detail and the mechanism governing nanostructures' transforming effect by surface treatment is exploited. In the end, it is summarized that the hierarchical polymerization combined with Ullmann coupling makes it possible to realize the selection of different synthetic pathways and phase transformations and obtain novel organometallic nanowire with metalorganic bonding.

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Self-assembly of pyrene derivatives on Au(111): substituent effects on intermolecular interactions

Abstract: The adsorption behaviour as well as the influence of bromine substituents on the formation of highly-ordered two-dimensional structures of pyrene derivatives on Au(111) are studied by a combination of scanning tunnelling microscopy (STM) and density functional theory (DFT) calculations.

Cited by 68 publications

References 23 publications

Halogen Bonding in Two‐Dimensional Crystal Engineering

Halogen Bonding in Two‐Dimensional Crystal Engineering

Comparing Ullmann Coupling on Noble Metal Surfaces: On‐Surface Polymerization of 1,3,6,8‐Tetrabromopyrene on Cu(111) and Au(111)

Recent Progress in the Fabrication of Low Dimensional Nanostructures via Surface-Assisted Transforming and Coupling

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