Synthesis of a peripherally conjugated 5-6-7 nanographene

Żyła, Marika; Gońka, Elżbieta; Chmielewski, Piotr J.; Cybińska, Joanna; Stępień, Marcin

doi:10.1039/c5sc03280f

Cited by 64 publications

(20 citation statements)

References 65 publications

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“…Stępień and co‐workers have synthesized an analogue of 177 with one pyrrole ring replaced by an indole unit ( 179 ; Figure ) . The cyclization was accomplished using tris(4‐bromophenyl)ammoniumyl hexachloroantimonate (BAHA, also known as “Magic Blue”), a radical cation oxidant.…”

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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“…Consequently, higher oxidation levels could be easily accessed and a tetracationic species 266 4+ could be generated by chemical oxidation with SbCl 5 . In 2016, the same group [326] reported a new derivative 267 containing a combination of 5-, 6-, and 7-membered rings by oxidative cyclodehydrogenation of an indole-containing precursor. The extended molecule displayed a lower HOMO-LUMO gap compared with the pristine hexapyrrolohexaazacoronene.…”

Section: Heteroatom Dopingmentioning

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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“…The emission spectra of all the compounds looked similar with three intense peaks at wavelengths of 410 nm, 436 nm, and 465 nm for 6 a‐d with high intense peak at around 436 nm for all four compounds. Though multiple peaks in the emission spectra are less common, they have been observed in similar systems ,,,. The Stokes shifts between the absorption excitation maxima and emission maxima, of around 66 nm were observed for 6 a‐d .…”

Section: Resultsmentioning

confidence: 78%

Novel Annulated Triphenylene Discotic Liquid Crystals Generated by Pictet‐Spengler Cyclization

et al. 2018

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Triphenylenes have been frontrunner in discotic liquid crystalline materials since their discovery. They possess great richness of mesomorphism in them. Chemists have been exploring this potential quite often by some substitutions in the core or periphery of the triphenylene molecule. In this current report, we extended the triphenylene ring system by fusing with nitrogen and studied their mesomorphic and optical properties. Four new compounds are prepared using Pictet‐Spengler cyclization of hexaalkoxytriphenylene‐1‐amine with various aldehydes. All the new compounds are well characterized using spectral and elemental analysis. Their mesomorphic properties are evaluated using polarizing optical microscopy, differential scanning calorimetry and X‐ray diffractometry. These derivatives showed columnar hexagonal phase with great promise for further studies.

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Synthesis of a peripherally conjugated 5-6-7 nanographene

Abstract: Expansion of heteroaromatic nanographenes via 5-6-7 fusion enhances their NIR absorption and emission properties.

Cited by 64 publications

References 65 publications

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

Polycyclic aromatic hydrocarbons in the graphene era

Novel Annulated Triphenylene Discotic Liquid Crystals Generated by Pictet‐Spengler Cyclization

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