On-surface radical addition of triply iodinated monomers on Au(111)—the influence of monomer size and thermal post-processing

Schlögl, Stefan; Heckl, Wolfgang M.; Lackinger, Markus

doi:10.1016/j.susc.2012.02.011

Cited by 51 publications

(60 citation statements)

References 22 publications

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“…This is consistent with previous studies showing that aryl radicals with increasing size on Au(111) require a continuous increase in temperature to facilitate surface diffusion and subsequent homo-coupling. 45,49,53,46,54 These results highlight the importance of understanding molecular diffusion in addition to the dissociation behavior of halogen substituents in order to perform rational on-surface synthesis.…”

Section: Summary and Discussionmentioning

confidence: 94%

Iodine versus Bromine Functionalization for Bottom-Up Graphene Nanoribbon Growth: Role of Diffusion

et al. 2017

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Deterministic bottom-up approaches for synthesizing atomically well-defined graphene nanoribbons (GNRs) largely rely on the surface-catalyzed activation of selected labile bonds in a molecular precursor followed by step growth polymerization and cyclodehydrogenation. While the majority of successful GNR precursors rely on the homolytic cleavage of thermally labile CBr bonds, the introduction of weaker C-I bonds provides access to monomers that can be polymerized at significantly lower temperatures, thus helping to increase the flexibility of the GNR synthesis process. Scanning tunneling microscopy (STM) imaging of molecular precursors, activated intermediates, and polymers resulting from stepwise thermal annealing of both Br and I substituted precursors for chevron GNRs reveals that the polymerization of both precursors proceeds at similar temperatures on Au(111). This observation is consistent with diffusionlimited polymerization of the surface-stabilized radical intermediates that emerge from homolytic cleavage of either the C-Br or the C-I bonds.3

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Section: Summary and Discussionmentioning

confidence: 94%

Iodine versus Bromine Functionalization for Bottom-Up Graphene Nanoribbon Growth: Role of Diffusion

et al. 2017

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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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“…The thereby generated surface-stabilized radicals diffuse and couple through C-C bond formation into covalent nanostructures. Depending on the type of metal surface, coupling proceeds either directly [2][3][4][5] or via a metastable organometallic intermediate. [6][7][8][9] As a noteworthy exception to this commonly observed scheme, we present the surface chemistry of 1,3-diiodobenzene (DIB, Fig.…”

Section: Ullmann Coupling Of 13-diiodobenzene Is Studied On Cu(111) mentioning

confidence: 99%

1,3-Diiodobenzene on Cu(111) – an exceptional case of on-surface Ullmann coupling

et al. 2015

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On-surface radical addition of triply iodinated monomers on Au(111)—the influence of monomer size and thermal post-processing

Cited by 51 publications

References 22 publications

Iodine versus Bromine Functionalization for Bottom-Up Graphene Nanoribbon Growth: Role of Diffusion

Iodine versus Bromine Functionalization for Bottom-Up Graphene Nanoribbon Growth: Role of Diffusion

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

1,3-Diiodobenzene on Cu(111) – an exceptional case of on-surface Ullmann coupling

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