Iodobenzene on Cu(111): formation and coupling of adsorbed phenyl groups

Xi, Ming; Bent, Brian E.

doi:10.1016/0039-6028(92)90580-y

Cited by 133 publications

(149 citation statements)

References 39 publications

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“…Di-iodobenzene adsorption was performed with the graphite substrates cooled to 110 K, where C-I bond scission is unlikely [22][23][24][25], under ultra-high vacuum (UHV) conditions. The clean graphite surface was characterized by core level X-ray photoemission (XPS), and combined valence band photoemission and inverse photoemission, as described elsewhere [29].…”

Section: Methodsmentioning

confidence: 99%

“…By avoiding surface steps we minimize the number of adsorbate interactions at step edges. The weak influence of the graphite substrate with the adsorbate is important in suppressing adsorbate dissociation, particularly as dehalogenation, seen with halogenated benzene adsorption, occurs on many substrates [17][18][19][20], but does not occur with initial halogenated benzene adsorption on some select metal [21][22][23][24][25] and nonmetallic substrates [26][27][28].…”

Section: Introductionmentioning

confidence: 99%

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Isomeric effects with di-iodobenzene (C6H4I2) on adsorption on graphite

Fukutani

Dowben

2009

Surface Science

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Isomeric effects with di-iodobenzene (C6H4I2) on adsorption on graphite

Fukutani

Dowben

2009

Surface Science

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“…On surfaces, extensive work on alkyl coupling has been reported by Bent et al on copper [9,[121][122][123] and gold [124,125] surfaces, and by White et al on silver [126]. Other metals often favor dehydrogenation steps instead, b-hydride elimination in particular, but can sometimes be passivated with coadsorbed atoms such as oxygen to favor the coupling route.…”

Section: Reductive Eliminationsmentioning

confidence: 95%

Mechanisms of hydrocarbon conversion reactions on heterogeneous catalysts: analogies with organometallic chemistry

Zaera

2005

Top Catal

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Catalysis is central to most industrial processes for chemical manufacturing. As catalytic processes have become more complex and more demanding, selectivity has become the central issue in their design. Selectivity is defined by the relative rates of competing reaction pathways available to crucial intermediates, and can be controlled by subtle changes in the nature of the catalyst, the reactants, and/or the reaction conditions. In order to be able to do this in a systematic manner, a good understanding of the catalytic reaction mechanisms is needed. Here a connection is drawn between the key elementary steps comprising hydrocarbon conversion reactions on surfaces and those known to occur on discrete organometallic complexes. This way, the hydrogenation, dehydrogenation, hydrogenolysis, chain growth, and isomerization reactions typical in heterogeneous catalysis are redefined in terms of hydride elimination, oxidative addition, reductive elimination, migratory insertion, and . 1, 2-shift elementary steps, among others. It is suggested that the knowledge already available from organometallic chemistry can be used to further advance the understanding of the surface science involved in heterogeneous catalysis. Thanks to the commonality of the chemistry involved, a better synergy could also be established between homogeneous and heterogeneous catalytic development. These ideas are discussed in this article in a critical and personal way.

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“…Traditional Ullmann coupling reactions were pioneered by the work of Fritz Ullmann and Irma Goldberg in the early 1900s [64], and the solutionphase Ullmann coupling reaction was originally developed as a C−C coupling between aromatic halides induced by copper or Cu halide, a trend which continued to the end of 20th century. Afterwards, this type of coupling was transferred to solid surfaces (mostly coinage metals) in UHV for on-surface synthesis of 1D and 2D polymers [65], and the mechanism of the classical solution-phase Ullmann coupling reaction mechanism ( -bond metathesis [66]) and the later reaction mechanism may be substrate-and molecule-dependent, also because the necessary reaction conditions vary with the substrate [67]. Two typical mechanisms are displayed in Figure 7.…”

Section: Ullmann Reaction and The Optimization Of Hierarchicalmentioning

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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Iodobenzene on Cu(111): formation and coupling of adsorbed phenyl groups

Cited by 133 publications

References 39 publications

Isomeric effects with di-iodobenzene (C6H4I2) on adsorption on graphite

Isomeric effects with di-iodobenzene (C6H4I2) on adsorption on graphite

Mechanisms of hydrocarbon conversion reactions on heterogeneous catalysts: analogies with organometallic chemistry

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

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