[7.7]Circulene, a Molecule Shaped Like a Figure of Eight

Yamamoto, Kōji; Saitho, Yasuhiro; Iwaki, Daisuke; Ôoka, Takayuki

doi:10.1002/anie.199111731

Cited by 71 publications

(25 citation statements)

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“…Moreover, [7]circulene and [8]circulene can be regarded as graphene molecules containing seven-and eight-membered rings, respectively. 123 Nevertheless, graphene molecules with embedded seven-membered rings, other than the circulenes, had remained elusive. 123 Nevertheless, graphene molecules with embedded seven-membered rings, other than the circulenes, had remained elusive.…”

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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“…Accordingly, corannulene 17 and coronene 43 can be regarded as [5]circulene and [6]circulene, respectively. [7]Circulene was initially synthesized by Yamamoto and Nakazaki et al in 1983 [277], and the synthesis of [7.7]circulene, which had two seven-membered rings, was reported in 1991 [278]. Other than circulenes, limited examples of nanographene molecules with embedded sevenmembered rings are available.…”

Section: "Defects" Make the Differencementioning

confidence: 99%

Polycyclic aromatic hydrocarbons in the graphene era

2019

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Polycyclic aromatic hydrocarbons (PAHs) have been the subject of interdisciplinary research in the fields of chemistry, physics, materials science, and biology. Notably, PAHs have drawn increasing attention since the discovery of graphene, which has been regarded as the "wonder" material in the 21st century. Different from semimetallic graphene, nanoscale graphenes, such as graphene nanoribbons and graphene quantum dots, exhibit finite band gaps owing to the quantum confinement, making them attractive semiconductors for next-generation electronic applications. Researches based on PAHs and graphenes have expanded rapidly over the past decade, thereby posing a challenge in conducting a comprehensive review. This study aims to interconnect the fields of PAHs and graphenes, which have mainly been discussed separately. In particular, by selecting representative examples, we explain how these two domains can stimulate each other. We hope that this integrated approach can offer new opportunities and further promote synergistic developments in these fields.

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“…Nanographene with an embedded three‐dimensional, negative Gaussian curvature represents a new class of nanocarbons, which are considered to be next‐generation carbon materials . Due to their saddle‐shaped skeletons, negatively curved nanographenes exhibit relatively weak intermolecular π–π interactions and good solubility in organic solvents; they also possess interesting nonlinear optical and electrochemical properties.…”

Section: Figurementioning

confidence: 99%

A Water‐Soluble Warped Nanographene: Synthesis and Applications for Photoinduced Cell Death

et al. 2018

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Nanographene, a small piece of graphene, has attracted unprecedented interest across diverse scientific disciplines particularly in organic electronics. The biological applications of nanographenes, such as bioimaging, cancer therapies and drug delivery, provide significant opportunities for breakthroughs in the field. However, the intrinsic aggregation behavior and low solubility of nanographenes, which stem from their flat structures, hamper their development for bioapplications. Herein, we report a water-soluble warped nanographene (WNG) that can be easily synthesized by sequential regioselective C-H borylation and cross-coupling reactions of the saddle-shaped WNG core structure. The saddle-shaped structure and hydrophilic tetraethylene glycol chains impart high water solubility to the WNG. The water-soluble WNG possesses a range of promising properties including good photostability and low cytotoxicity. Moreover, the water-soluble WNG was successfully internalized into HeLa cells and promoted photoinduced cell death.

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[7.7]Circulene, a Molecule Shaped Like a Figure of Eight

Abstract: ters, full-matrix least-squares refinement, SHELX76 program [I 11. R = 0.0286, R, = 0.0326. Weighting scheme: n = k/[a2(F) + g PI, with k = 3.2061 and g = 0.000183. Crystal data for 1 b: monoclinic. Cc, a = 15.084(2),b= 10.414(2),~= 13.844(2) A,B= 109.07(1)", V=2055.3(6)A3,

Cited by 71 publications

References 4 publications

New advances in nanographene chemistry

New advances in nanographene chemistry

Polycyclic aromatic hydrocarbons in the graphene era

A Water‐Soluble Warped Nanographene: Synthesis and Applications for Photoinduced Cell Death

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