Bending contorted hexabenzocoronene into a bowl

Whalley, Adam C.; Plunkett, Kyle N.; Gorodetsky, Alon A.; Schenck, Christine L.; Chiu, Chien‐Yang; Steigerwald, Michael L.; Nuckolls, Colin

doi:10.1039/c0sc00470g

Cited by 70 publications

(62 citation statements)

References 23 publications

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“…85 This synthetic protocol can be applied to other (arylethynyl)benzene derivatives, 86 providing potential access to previously unavailable graphene molecules, including contorted species with open bonds at selective positions. Notably, PAH 5b exhibited enhanced visible absorption compared with that of fully fused graphene molecule 6a, with an optical gap of 2.32 eV derived from its UV-Vis absorption spectrum.…”

Section: Synthesis Of Graphene Moleculesmentioning

confidence: 99%

New advances in nanographene chemistry

et al. 2015

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Nanographenes, or extended polycyclic aromatic hydrocarbons, have been attracting renewed and more widespread attention since the first experimental demonstration of graphene in 2004. However, the atomically precise fabrication of nanographenes has thus far been achieved only through synthetic organic chemistry. The precise synthesis of quasi-zero-dimensional nanographenes, i.e. graphene molecules, has witnessed rapid developments over the past few years, and these developments can be summarized in four categories: (1) non-conventional methods, (2) structures incorporating seven- or eight-membered rings, (3) selective heteroatom doping, and (4) direct edge functionalization. On the other hand, one-dimensional extension of the graphene molecules leads to the formation of graphene nanoribbons (GNRs) with high aspect ratios. The synthesis of structurally well-defined GNRs has been achieved by extending nanographene synthesis to longitudinally extended polymeric systems. Access to GNRs thus becomes possible through the solution-mediated or surface-assisted cyclodehydrogenation, or "graphitization," of tailor-made polyphenylene precursors. In this review, we describe recent progress in the "bottom-up" chemical syntheses of structurally well-defined nanographenes, namely graphene molecules and GNRs.

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Section: Synthesis Of Graphene Moleculesmentioning

confidence: 99%

New advances in nanographene chemistry

et al. 2015

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“…2) were recently studied by Nuckolls, and coworkers. [14] From an experimental point of view, these authors pointed to the structural diversity of these compounds obtained by closure of the five‐membered rings around the exterior of hexabenzocoronene.…”

Section: Introductionmentioning

confidence: 99%

Conjugated circuits currents in hexabenzocoronene and its derivatives formed by joining proximal carbons

et al. 2012

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We report on calculated CC bond currents for a dozen derivatives of hexabenzocoroenene in which one or more proximal carbon atoms at the molecular periphery have been bridged. The approach that we use is graph-theoretical in nature, following our outline of this method in 2003, which is based on finding all conjugated circuits in all Kekulé valence structures of these molecules. To the π-electrons having 4n + 2 π-electrons are assigned anticlockwise π-electron currents and to conjugated circuits having 4n π-electrons are assigned π-electron currents. One may summarize the results reported in this work by stating that CC bond currents in the compounds considered decrease on going from peripheral rings to the central ring of the molecule, and also that CC bond currents decrease by insertion of bridges to proximal peripheral benzenoid rings.

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“…Buckybowl 169 is not a fragment of common fullerenes, such as C 60 and C 70 (Scheme 53) [178]. The synthesis started with pentacenequinone 167, and the final step was microwave-assisted Pd-catalyzed cyclization of 168.…”

Section: Hexabenzocoronene-based Buckybowlmentioning

confidence: 99%

Synthesis, Structures, and Physical Properties of Aromatic Molecular-Bowl Hydrocarbons

Siegel

2014

Topics in Current Chemistry

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This chapter summarizes the synthesis, physical properties, structure, and crystal packing of buckybowls. Buckybowls exemplify an intermediate class of polynuclear aromatic compounds between the closed-shell fullerenes and the flat extended arrays of graphene. These warped sheets can be seen as fragments of fullerenes or the end cap of single-walled carbon nanotubes; and, their curvature endows them with physical properties distinct from flat polynuclear hydrocarbons, which opens up unique possibilities for molecular bowls in various organic materials applications.

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Bending contorted hexabenzocoronene into a bowl

Cited by 70 publications

References 23 publications

New advances in nanographene chemistry

New advances in nanographene chemistry

Conjugated circuits currents in hexabenzocoronene and its derivatives formed by joining proximal carbons

Synthesis, Structures, and Physical Properties of Aromatic Molecular-Bowl Hydrocarbons

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