Chemistry of 4-[(4-bromophenyl)ethynyl]pyridine at metal surfaces studied by STM

Ren, Jinjun; Larkin, Eugene; Delaney, Colm; Song, Yang; Jin, Xin; Amirjalayer, Saeed; Bakker, Anne; Du, Shixuan; Gao, Hailing; Zhang, Yuyang; Draper, Sylvia M.; Fuchs, Harald

doi:10.1039/c8cc03986k

Cited by 23 publications

(21 citation statements)

References 21 publications

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“…In addition, a powerful experimental method to reversibly switch [37] the conformations and their accompanying self‐assembly of cyCAAC is displayed. To learn the importance of cyCAAC‐surface interactions on monolayer structures, [38] Ag (111) and Cu (111) are also chosen as substrates. The ballbot‐like species of the cyCAAC on Au (111) does not appear on Ag (111) and Cu (111).…”

Section: Introductionmentioning

confidence: 99%

Reversible Self‐Assembly of an N‐Heterocyclic Carbene on Metal Surfaces

et al. 2022

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Self‐assembly of cyclohexyl cyclic (alkyl)(amino)carbenes (cyCAAC) can be realized and reversibly switched from a close‐packed trimer phase to a chainlike dimer phase, enabled by the ring‐flip of the cyclohexyl wingtip. Multiple methods including scanning tunneling microscopy (STM), X‐ray photoelectron spectroscopy (XPS) and density functional theory (DFT) calculations identified a distinct isomer (axial or equatorial chair conformer) in each phase, and consequently support the conclusion regarding the determination of molecular surface geometry on the self‐assembly of cyCAAC. Moreover, various substrates such as Ag (111) and Cu (111) are tested to elucidate the importance of cyCAAC‐surface interactions on cyCAAC based nanopatterns. These investigations of patterned surfaces prompted a deep understanding of cyCAAC binding mode, surface geometry and reversible self‐assembly, which are of paramount significance in the areas of catalysis, biosensor design and surface functionalization.

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Section: Introductionmentioning

confidence: 99%

Reversible Self‐Assembly of an N‐Heterocyclic Carbene on Metal Surfaces

et al. 2022

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“…The high-resolutionS TM image revealed the molecular arrangement depicted in Figure 1e.B etween the molecules ac ircular protrusion connecting the adjacent molecular units could be distinguished and ascribed to Cu adatoms. [16] The angle of 1808 at the connecting moieties supported the assumption that the CÀOb ond was cleaved leadingt oa ryl radicals R2 ( Figure 1f)c onnected by adatoms. Unlike reporteda ryloxy radical CÀCc ouplings on Au(111)a nd Ag(111), [15] deoxygenation of the aryloxy radicalo nC u(111)i s faster than ortho homocoupling.T he existence of Cu adatom stabilized radicals R2 was further supportedb yd istance measurement betweent wo central benzene rings in the observed STM line profile, whichw as measured to be 1.49 AE 0.05 nm fitting the proposed structure well ( Figure S4).…”

Section: Resultsmentioning

confidence: 53%

“…The high‐resolution STM image revealed the molecular arrangement depicted in Figure 1 e. Between the molecules a circular protrusion connecting the adjacent molecular units could be distinguished and ascribed to Cu adatoms [16] . The angle of 180° at the connecting moieties supported the assumption that the C−O bond was cleaved leading to aryl radicals R2 (Figure 1 f) connected by adatoms.…”

Section: Resultsmentioning

confidence: 71%

Aryl Triflates in On‐Surface Chemistry

Ren

Klaasen

Witteler

et al. 2020

Chemistry A European J

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The reactivity of aryl triflates in on‐surface C−C coupling is reported. It is shown that the triflate group in aryl triflates enables regioselective homo coupling with preceding or concomitant hydrodetriflation on Cu(111). Three different symmetrical π‐systems with two and three triflate functionalities were used as monomers leading to oligomeric conjugated π‐systems. The cascade, comprising different intermediates at different reaction temperatures as observed for one of the molecules, proceeds via initial removal of the trifluoromethyl sulfonyl group to give an aryloxy radical which in turn is deoxygenated to the corresponding aryl radical. Thermodynamically driven regioselective 1,2‐hydrogen atom transfer leads to a translocated aryl radical which in turn undergoes coupling. For a sterically more hindered bistriflate, where one ortho position was blocked, dehydrogenative coupling occurred at remote position with good regioselectivity. Starting materials, intermediates as well as products were analyzed by scanning tunneling microscopy. Structures and suggested mechanism were further supported by DFT calculations.

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“…There are various molecules that possess the ability to selfassemble on solid surfaces. One of the most interesting types are building blocks of linear [8][9][10][11][12], V-shape [13,14], tripod [15,16], tetrapod [17][18][19][20][21], and hexapod [22] architecture. Also, a lot of effort has been put into the investigation of the mixtures [23][24][25] and the guest-induced self-assembly [26] of aforementioned particles.…”

Section: Introductionmentioning

confidence: 99%

Simulations of the 2D self-assembly of tripod-shaped building blocks

Baran

Rżysko

Słyk

2020

Beilstein J. Nanotechnol.

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We introduce a molecular dynamics (MD) coarse-grained model for the description of tripod building blocks. This model has been used by us already for linear, V-shape, and tetratopic molecules. We wanted to further extend its possibilities to trifunctional molecules to prove its versatility. For the chosen systems we have also compared the MD results with Monte Carlo results on a triangular lattice. We have shown that the constraints present in the latter method can enforce the formation of completely different structures, not reproducible with off-lattice simulations. In addition to that, we have characterized the obtained structures regarding various parameters such as theoretical diffraction pattern and average association number.

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Chemistry of 4-[(4-bromophenyl)ethynyl]pyridine at metal surfaces studied by STM

Cited by 23 publications

References 21 publications

Reversible Self‐Assembly of an N‐Heterocyclic Carbene on Metal Surfaces

Reversible Self‐Assembly of an N‐Heterocyclic Carbene on Metal Surfaces

Aryl Triflates in On‐Surface Chemistry

Simulations of the 2D self-assembly of tripod-shaped building blocks

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