Exploring Intramolecular Methyl–Methyl Coupling on a Metal Surface for Edge-Extended Graphene Nanoribbons

Qiu, Zijie; Sun, Qiang; Wang, Shiyong; Barin, Gabriela Borin; Dumslaff, Bastian; Ruffieux, Pascal; Müllen, Kläus; Narita, Akimitsu; Fasel, Román

doi:10.1055/s-0041-1726295

Cited by 3 publications

(1 citation statement)

References 44 publications

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“…The formation of such NGs is attributed to the oxidative ring closure of the majority of the methyl groups, together with the dissociation of several of them per NG prior to cyclization. Such removal of methyl moieties was previously reported in the synthesis of several NGs [30,37,[42][43][44][45] and GNRs [22,46] and is concomitant to the annealing step at temperatures where the oxidative ring closure is expected to occur on Au(111), therefore being not possible to achieve the synthesis of E.…”

Section: On-surface Synthesis Of Non-benzenoid Nanographenesmentioning

confidence: 85%

Defect-Induced π-Magnetism into Non-Benzenoid Nanographenes

Biswas

Yang

et al. 2022

Nanomaterials

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The synthesis of nanographenes (NGs) with open-shell ground states have recently attained increasing attention in view of their interesting physicochemical properties and great prospects in manifold applications as suitable materials within the rising field of carbon-based magnetism. A potential route to induce magnetism in NGs is the introduction of structural defects, for instance non-benzenoid rings, in their honeycomb lattice. Here, we report the on-surface synthesis of three open-shell non-benzenoid NGs (A1, A2 and A3) on the Au(111) surface. A1 and A2 contain two five- and one seven-membered rings within their benzenoid backbone, while A3 incorporates one five-membered ring. Their structures and electronic properties have been investigated by means of scanning tunneling microscopy, noncontact atomic force microscopy and scanning tunneling spectroscopy complemented with theoretical calculations. Our results provide access to open-shell NGs with a combination of non-benzenoid topologies previously precluded by conventional synthetic procedures.

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Section: On-surface Synthesis Of Non-benzenoid Nanographenesmentioning

confidence: 85%

Defect-Induced π-Magnetism into Non-Benzenoid Nanographenes

Biswas

Yang

et al. 2022

Nanomaterials

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Mechanosynthesis of graphene nanoribbons from waste zinc–carbon batteries

et al. 2021

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On-surface cyclization of vinyl groups on poly-para-phenylene involving an unusual pentagon to hexagon transformation

Di Giovannantonio,

Qiu,

Pignedoli

et al. 2024

Nat Commun

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On-surface synthesis relies on carefully designed molecular precursors that are thermally activated to afford desired, covalently coupled architectures. Here, we study the intramolecular reactions of vinyl groups in a poly-para-phenylene-based model system and provide a comprehensive description of the reaction steps taking place on the Au(111) surface under ultrahigh vacuum conditions. We find that vinyl groups successfully cyclize with the phenylene rings in the ortho positions, forming a dimethyl-dihydroindenofluorene as the repeating unit, which can be further dehydrogenated to a dimethylene-dihydroindenofluorene structure. Interestingly, the obtained polymer can be transformed cleanly into thermodynamically stable polybenzo[k]tetraphene at higher temperature, involving a previously elusive pentagon-to-hexagon transformation via ring opening and rearrangement on a metal surface. Our insights into the reaction cascade unveil fundamental chemical processes involving vinyl groups on surfaces. Because the formation of specific products is highly temperature-dependent, this innovative approach offers a valuable tool for fabricating complex, low-dimensional nanostructures with high precision and yield.

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Exploring Intramolecular Methyl–Methyl Coupling on a Metal Surface for Edge-Extended Graphene Nanoribbons

Cited by 3 publications

References 44 publications

Defect-Induced π-Magnetism into Non-Benzenoid Nanographenes

Defect-Induced π-Magnetism into Non-Benzenoid Nanographenes

Mechanosynthesis of graphene nanoribbons from waste zinc–carbon batteries

On-surface cyclization of vinyl groups on poly-para-phenylene involving an unusual pentagon to hexagon transformation

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