Closing the Nanographene Gap: Surface‐Assisted Synthesis of Peripentacene from 6,6′‐Bipentacene Precursors

Rogers, Christopher L.; Chen, Chen; Pedramrazi, Zahra; Omrani, Arash A.; Tsai, Hsin‐Zon; Jung, Han Sae; Lin, Song; Crommie, Michael F.; Fischer, Felix R.

doi:10.1002/ange.201507104

Cited by 49 publications

(20 citation statements)

References 42 publications

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“…Since its introduction at the turn of the 21st century, the on-surface synthesis approach has proven to be extremely successful in providing functional nanomaterials, whose structure could be controlled down to even single atoms. 1 Over the past several years, the surface-assisted nanomaterial synthesis has attracted tremendous researcher attention as an alternative to conventional solution chemistry, being particularly effective in the generation of polymers, 2 graphene nanoribbons, 3 , 4 nanoflakes, 5 − 8 or elusive single molecules. 9 − 11 The approach enables precise synthesis of molecular nanoarchitectures exhibiting the desired structural, chemical, electronic, and magnetic properties 11 using custom designed molecular precursors.…”

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confidence: 99%

On-Surface Synthesis with Atomic Hydrogen

et al. 2020

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Surface-assisted synthesis has become a powerful approach for generation of molecular nanostructures, which could not be obtained via traditional solution chemistry. Nowadays there is an intensive search for reactions that could proceed on flat surfaces in order to boost the versatility and applicability of synthesized nano-objects. Here we propose application of atomic hydrogen combined with on-surface synthesis in order to tune the reaction pathways. We demonstrate that atomic hydrogen could be widely applied: (1) as a cleaning tool, which allows removal of halogen residues from the surface after Ullmann couplings/polymerization, (2) by reaction with surface organometallics to provide stable hydrogenated species, and (3) as a reagent for debromination or desulfurization of adsorbed species.

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confidence: 99%

On-Surface Synthesis with Atomic Hydrogen

et al. 2020

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“…In this regard, modern on-surface chemistry serves as a powerful synthetic tool toward bottom-up fabrication of complex nanostructures unattainable via solution chemistry 29 . Many challenging syntheses of carbon-based nanostructures have been realized through this approach including atomically precise graphene nanoribbons 30 , single-chirality single-walled carbon nanotubes 31 , longest to-date acenes 32 and periacenes 33 , and embedment of non-hexagonal rings in PAHs 34 .…”

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confidence: 99%

On-surface synthesis of a nitrogen-embedded buckybowl with inverse Stone–Thrower–Wales topology

et al. 2018

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Curved π-conjugated polycyclic aromatic hydrocarbons, buckybowls, constitute an important class of materials with wide applications in materials science. Heteroatom doping of buckybowls is a viable route to tune their intrinsic physicochemical properties. However, synthesis of heteroatom-doped buckybowls is a challenging task. We report on a combined in-solution and on-surface synthetic strategy toward the fabrication of a buckybowl containing two fused nitrogen-doped pentagonal rings. We employ ultra-high-resolution scanning tunneling microscopy and spectroscopy, in combination with density functional theory calculations to characterize the final compound. The buckybowl contains a unique combination of non-hexagonal rings at its core, identified as the inverse Stone–Thrower–Wales topology, resulting in a distinctive bowl-opening-down conformation of the buckybowl on the surface. Our controlled design of non-alternant, heteroatom-doped polycyclic aromatic frameworks with established bottom-up fabrication techniques opens new opportunities in the synthesis of carbon nanostructures with the perspective of engineering properties of graphene-based devices.

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“…Together with the advent of graphene science, an important chapter in organic chemistry has opened exploring the synthesis of extended polycyclic aromatic hydrocarbon (PAH) systems. Large PAHs, as represented by hexa- peri -hexabenzocoronene (HBC, 1 ) with π-conjugated structures extending over 1 nm, can be regarded as structurally defined, nanoscale cutouts of graphene, designated nanographene molecules 1 – 3 . Such systems can serve as platforms both for investigating the physical and chemical properties of graphene upon heteroatom-doping, as well as for the development of semiconducting materials (see Fig.…”

Section: Introductionmentioning

confidence: 99%

Exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine ylide homocoupling

Wang

Richter

et al. 2017

Nat Commun

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Nanographenes, namely polycyclic aromatic hydrocarbons (PAHs) with nanoscale dimensions (>1 nm), are atomically precise cutouts from graphene. They represent prime models to enhance the scope of chemical and physical properties of graphene through structural modulation and functionalization. Defined nitrogen doping in nanographenes is particularly attractive due to its potential for increasing the number of π-electrons, with the possibility of introducing localized antiaromatic ring elements. Herein we present azomethine ylide homocoupling as a strategy to afford internally nitrogen-doped, non-planar PAH in solution and planar nanographene on surfaces, with central pyrazine rings. Localized antiaromaticity of the central ring is indicated by optical absorption spectroscopy in conjunction with theoretical calculations. Our strategy opens up methods for chemically tailoring graphene and nanographenes, modified by antiaromatic dopants.

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Closing the Nanographene Gap: Surface‐Assisted Synthesis of Peripentacene from 6,6′‐Bipentacene Precursors

Cited by 49 publications

References 42 publications

On-Surface Synthesis with Atomic Hydrogen

On-Surface Synthesis with Atomic Hydrogen

On-surface synthesis of a nitrogen-embedded buckybowl with inverse Stone–Thrower–Wales topology

Exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine ylide homocoupling

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