Contorted polycyclic aromatic hydrocarbons with cove regions and zig-zag edges

Chen, Yulan; Marszałek, Tomasz; Fritz, Torsten; Baumgarten, Martin; Wagner, Manfred; Pisula, Wojciech; Chen, Long; Müllen, Kläus

doi:10.1039/c7cc03709k

Cited by 47 publications

(16 citation statements)

References 29 publications

(20 reference statements)

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“…Müllen, Chen, and co‐workers have reported the synthesis of a series of tetrapyrene‐fused benzocoronenes 150 a – c (Figure ) . All compounds were obtained in very good yields by the FeCl 3 ‐mediated oxidation of the corresponding tetrapyrenylpentacene‐quinodimethanes.…”

Section: Intramolecular Oxidative Aromatic Couplingmentioning

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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Section: Intramolecular Oxidative Aromatic Couplingmentioning

confidence: 99%

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

et al. 2019

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“…Müllen, Chen et al. haben über die Synthese einer Reihe von Tetrapyren‐kondensierten Benzocoronenen 150 a – c berichtet (Abbildung ) . Alle Verbindungen wurden in sehr guten Ausbeuten durch FeCl 3 ‐vermittelte Oxidation der entsprechenden Tetrapyrenylpentacen‐Chinodimethane erhalten.…”

Section: Intramolekulare Oxidative Aromatische Kupplungunclassified

Syntheseanwendungen der oxidativen aromatischen Kupplung – von Biphenolen zu Nanographenen

et al. 2019

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Die oxidative aromatische Kupplung nimmt einen grundlegenden Platz in der modernen Arenchemie ein. Sie ist das Mittel der Wahl für den Aufbau großer, komplizierter Molekülarchitekturen. Auch die Scholl‐Reaktion und ihre Anwendungen in der Synthese chiraler Biphenole und Naturstoffe sind stark beforscht. Die Möglichkeit, Biarylverknüpfungen ohne Vorfunktionalisierung herzustellen, bietet einen effizienten Weg zu vielen komplexen Strukturen. Obwohl die Chemie hinter diesem Prozess erst jetzt nach und nach voll verstanden wird, ist er weiterhin eine Quelle der Inspiration. Dies trifft besonders auf Heterokupplungen zu, d. h. oxidative, aromatische Kupplungen unter chemoselektiver C‐C‐Bindungsbildung zwischen zwei verschiedenen Arenen. Eine Analyse der Fortschritte in diesem Feld seit 2013 zeigt, dass zahlreiche Gruppen hierzu beigetragen haben – durch die Entdeckung neuer struktureller Möglichkeiten, die Erweiterung zu oberflächengestützten (Cyclo)dehydrierungen und die Entwicklung neuer Reagenzien.

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“…However, this can lead to disadvantageous side effects, such as a low tendency to form single crystals. This is why for some of the larger polycyclic aromatics [24a,c] and heteroaromatics, e. g. N‐heteroacenes with more than 15 annulated rings, no crystal structure is available, although soluble derivatives with up to 30 linearly fused rings have been synthesized [27b,c,28] …”

Section: Introductionmentioning

confidence: 99%

Triptycene End‐Capping as Strategy in Materials Chemistry to Control Crystal Packing and Increase Solubility

Ueberricke

Mastalerz

2021

The Chemical Record

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In materials chemistry of polycyclic aromatic compounds (PACs) the kind of aggregation and the spatial arrangement of the π‐planes are of utmost importance, e. g. for charge transport properties. Unfortunately, controlling these during crystallization is not trivial. In the past decade, we have introduced one‐fold triptycene end‐capping of quinoxalinophenanthrophenazines (QPPs) and other related structures to overcome this problem. When two instead of one triptycene end‐caps are introduced, packing is largely suppressed, making typical PACs or pigments soluble in common organic solvents – which is another important property for such compounds to be processable from solution. In this account an overview of our research on using triptycene end‐capping as dual strategy is given.

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Contorted polycyclic aromatic hydrocarbons with cove regions and zig-zag edges

Abstract: Three tetrapyrene-fused benzocoronenes were synthesized by a “bottom-up” approach, which offers a facile access to extended polycyclic aromatic hydrocarbons with cove regions and zig-zag edges.

Cited by 47 publications

References 29 publications

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

Syntheseanwendungen der oxidativen aromatischen Kupplung – von Biphenolen zu Nanographenen

Triptycene End‐Capping as Strategy in Materials Chemistry to Control Crystal Packing and Increase Solubility

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