Big Is Beautiful−“Aromaticity” Revisited from the Viewpoint of Macromolecular and Supramolecular Benzene Chemistry

Watson, Mark D.; Fechtenkötter, and Andreas; Müllen, Kläus

doi:10.1021/cr990322p

Cited by 1,325 publications

(861 citation statements)

References 259 publications

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“…In all cases, the synthesis proceeded via cyclodehydrogenation (flattening) of suitably designed polyphenylene precursors. 35,36 Indeed, the precursor of nanographene 3 (C222) is compound 3', which turned out to be nothing more than a first-generation polyphenylene dendrimer with a hexaphenylbenzene core. In every case, the synergy between synthesis and STM studies proved to be of outstanding value.…”

Section: Graphene Molecules and Graphene Nanoribbonsmentioning

confidence: 99%

Evolution of Graphene Molecules: Structural and Functional Complexity as Driving Forces behind Nanoscience

2014

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Abstract:The evolution of nanoscience is based on the ability of the fields of chemistry and physics to share competencies through mutually beneficial collaborations. With this in mind, in this Perspective, I describe three classes of compounds: rylene dyes, polyphenylene dendrimers, as well as nanographene molecules and graphene nanoribbons, which have provided a superb platform to nurture these relationships. The synthesis of these complex structures is demanding, but also rewarding because they stimulate unique investigations at the singlemolecule level by scanning tunneling microscopy and single-molecule spectroscopy. There are close functional and structural relationships between the molecules chosen. In particular, rylenes and nanographenes can be regarded as honeycombtype, discoid species composed of fused benzene rings. The benzene ring can thus be regarded as a universal modular building block. Polyphenylene dendrimers serve, first, as a scaffold for dyes en route to multichromophoric systems and, second, as chemical precursors for graphene synthesis. Through chemical design, it is possible to tune the properties of these systems at the single-molecule level and to achieve nanoscale control over their self-assembly to form multifunctional (nano)materials.

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Section: Graphene Molecules and Graphene Nanoribbonsmentioning

confidence: 99%

Evolution of Graphene Molecules: Structural and Functional Complexity as Driving Forces behind Nanoscience

2014

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“…Stereo-views of [12]heliphene (side and front view). lar reactions (with higher yields in the presence of CuCl 2 which acts also as oxidant, in Kovacic-type reactions (dehydro coupling of aromatic rings [87]) have been carried out by Müllen and coworkers for obtaining experimentally large claromatic benzenoids [88].…”

Section: Intermolecular Dehydrogenation Productsmentioning

confidence: 99%

Heliphenes and Related Structures

Balaban

Vollhardt

2011

TOOCJ

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This review discusses from a qualitative viewpoint three-dimensional structures (hydrocarbons and carbon allotropes) that can be obtained from the 4,6,12-archimedean tiling of the Euclidean plane (graphenylene net) or that are related to subgraphs derived from the graphenylene net, insisting on helical structures called [n]heliphenes with alternating 4-and 6-membered conjugated rings. Analogies with benzenoid [n]helicenes allow proposals for non-planar heliphenerelated structures that have yet to be explored.

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“…[44][45][46] It has also been applied to graphene-related systems, 46,47 carbon nanotubes, [48][49][50] and to ribbons 51,52 to some extent.…”

Section: Introductionmentioning

confidence: 99%

Clar’s Theory, π-Electron Distribution, and Geometry of Graphene Nanoribbons

et al. 2010

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We show that Clar's theory of the aromatic sextet is a simple and powerful tool to predict the stability, the π-electron distribution, the geometry, the electronic/magnetic structure of graphene nanoribbons with different hydrogen edge terminations. We use density functional theory to obtain the equilibrium atomic positions, simulated scanning tunneling microscopy (STM) images, edge energies, band gaps, and edge-induced strains of graphene ribbons that we analyze in terms of Clar formulas. Based on their Clar representation, we propose a classification scheme for graphene ribbons that groups configurations with similar bond length alternations, STM patterns, and Raman spectra. Our simulations show how STM images and Raman spectra can be used to identify the type of edge termination.

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Big Is Beautiful−“Aromaticity” Revisited from the Viewpoint of Macromolecular and Supramolecular Benzene Chemistry

Cited by 1,325 publications

References 259 publications

Evolution of Graphene Molecules: Structural and Functional Complexity as Driving Forces behind Nanoscience

Evolution of Graphene Molecules: Structural and Functional Complexity as Driving Forces behind Nanoscience

Heliphenes and Related Structures

Clar’s Theory, π-Electron Distribution, and Geometry of Graphene Nanoribbons

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