Annularly Fused Hexapyrrolohexaazacoronenes: An Extended π System with Multiple Interior Nitrogen Atoms Displays Stable Oxidation States

Takase, Masayoshi; Enkelmann, Volker; Sebastiani, Daniel; Baumgarten, Martin; Müllen, Kläus

doi:10.1002/anie.200701452

Cited by 154 publications

(120 citation statements)

References 31 publications

(12 reference statements)

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“…Interestingly, HPHAC can be regarded as a fully benzene-fused hexaphyrin(0.0.0.0.0.0), and the dication appears to possess full aromaticity. [67] …”

Section: Template Synthesismentioning

confidence: 97%

Expanded Porphyrins: Intriguing Structures, Electronic Properties, and Reactivities

2011

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The chemistry of expanded porphyrins, which are higher homologues of porphyrins, has been intensively explored for the last three decades. Expanded porphyrins exhibit structures, electronic properties, coordination chemistry, and reactivities that are entirely different from those of porphyrins. Through these studies, it has become increasingly apparent that expanded porphyrins are attractive in views of aromaticity and multimetal coordination, or as functional dyes, nonlinear optical materials, ion receptors, or stable organic radicals. As such, we have continuously witnessed the emergence of expanded porphyrins that exhibit unprecedented structures and properties, as is highlighted by the facile realization of Möbius aromatic and even antiaromatic systems with twisted molecular structures. In this Review, the recent progress of the chemistry of expanded porphyrins after the seminal Review by Sessler and Seidel in 2003 is presented.

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“…Interestingly, HPHAC can be regarded as a fully benzene-fused hexaphyrin(0.0.0.0.0.0), and the dication appears to possess full aromaticity. [67] …”

Section: Template Synthesismentioning

confidence: 97%

Expanded Porphyrins: Intriguing Structures, Electronic Properties, and Reactivities

2011

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“…By contrast, bottom-up organic synthesis can provide structurally defined heteroatom-doped graphene fragments with perfect control not only of the size, periphery and substituent, but also of the doping concentration and position. 142,143 These PAHs incorporating electron-rich pyrrole-type nitrogens exhibited up to four reversible oxidation processes in the electrochemical measurements. 41,60,[139][140][141] As typical examples of nitrogen (N)-doped graphene molecules, we developed a series of pyrrole-fused azacoronenes 52-55 ( Fig.…”

Section: Heteroatom-doped 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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“…[182] Ap rominent example was provided in 2007 by Müllen and coworkers,who synthesized the rim-fused hexapyrrolylbenzene 177 (Figure 13). [183] Thee lectron-rich nature of pyrrole was evident by the fact that the FeCl 3 -mediated cyclization initially led to an overoxidized dicationic form of 177,w hich could be reduced to the neutral 177 with hydrazine.M ore recently,t he authors have extended this synthetic method to include analogues of 177 with one,t wo,o rt hree pyrrole moieties replaced by benzene units (e.g. 178).…”

Section: Dyes and Heterocyclic Polyarenesmentioning

confidence: 99%

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

et al. 2019

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Oxidative aromatic coupling occupies a fundamental place in the modern chemistry of aromatic compounds. It is a method of choice for the assembly of large and bewildering architectures. Considerable effort was also devoted to applications of the Scholl reaction for the synthesis of chiral biphenols and natural products. The ability to form biaryl linkages without any prefunctionalization provides an efficient pathway to many complex structures. Although the chemistry of this process is only now becoming fully understood, this reaction continues to both fascinate and challenge researchers. This is especially true for heterocoupling, that is, oxidative aromatic coupling with the chemoselective formation of a C−C bond between two different arenes. Analysis of the progress achieved in this field since 2013 reveals that many groups have contributed by pushing the boundary of structural possibilities, expanding into surface‐assisted (cyclo)dehydrogenation, and developing new reagents.

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Annularly Fused Hexapyrrolohexaazacoronenes: An Extended π System with Multiple Interior Nitrogen Atoms Displays Stable Oxidation States

Cited by 154 publications

References 31 publications

Expanded Porphyrins: Intriguing Structures, Electronic Properties, and Reactivities

Expanded Porphyrins: Intriguing Structures, Electronic Properties, and Reactivities

New advances in nanographene chemistry

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

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