Maßgeschneiderte Synthese von Graphennanostrukturen mit Zickzack‐Rändern

Liu, Junzhi; Feng, Xinliang

doi:10.1002/ange.202008838

Cited by 51 publications

(5 citation statements)

References 175 publications

(307 reference statements)

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“…PAHs with different edge structures exhibit considerably distinct physical and chemical properties. Particularly, PAHs with multiple zigzag edges are of interest due to their appealing properties such as low band gap and diverse spin states [3] . Some PAHs containing more than two zigzag edges have been synthesized, including phenalenyl, [4] triangulenes, [5] peri‐acenoacenes, [6] and circumarenes [7] .…”

Section: Figurementioning

confidence: 99%

Circumcoronenes

et al. 2023

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Circumcoronene, a hexagonal graphene fragment with six zigzag edges, has been the focus of theoretical studies for many years, but its synthesis in solution has remained a challenge. In this study, we present a facile method for synthesizing three derivatives of circumcoronene using Brønsted/Lewis acidmediated cyclization of vinyl ether or alkyne. Their structures were confirmed through X-ray crystallographic analysis. Bond length analysis, NMR measurement, and theoretical calculations showed that circumcoronene mostly follows Clar's bonding model and exhibits dominant local aromaticity. Its absorption and emission spectra are similar to those of the smaller hexagonal coronene due to its six-fold symmetry.

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Section: Figurementioning

confidence: 99%

Circumcoronenes

et al. 2023

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“…Although the cross‐coupled precursor was isolated, during condensation, a substantial number of side‐products by Cannizarro disproportionation occurred making the isolation of PO‐17 impossible. However, since PO‐17 is formed and was detected by MS, further endeavors are currently made in our lab to synthesize higher members of this fascinating new PAHs (or graphene nanoribbons) [21] and study their materials properties as well as their chemistry more detailed.…”

Section: Discussionmentioning

confidence: 99%

Benzo‐Fused Perylene Oligomers with up to 13 Linearly Annulated Rings

2021

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The longer acenes with more than six linearly fused six‐membered rings are still fascinating chemists and physicists because of their unique photophysical properties and their high potential for organic electronics applications. Unfortunately, with increasing size (seven and more rings) these compounds rapidly lose chemical stability. Besides kinetic and chemical stabilization approaches introducing either bulky or electron‐withdrawing groups or both, such systems also have been stabilized by peri‐annulation. Although strictly spoken, these peri‐annulated compounds are no longer real acenes, they have fascinating properties as well. Herein, we describe the first synthesis of a new series of peri‐annulated acenes with up to 13 linearly fused rings, which is unprecedented till date. Furthermore, this new series contains perylene units connected through benzene rings along their [b,k]edges, responsible for unique absorption and emission properties.

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“…Circumarenes, a unique class of nanographenes (NGs) characterized by a distinctive zig-zag edge, feature a central aro-matic core surrounded by one outer layer of fused benzenoid rings. [1][2][3] Among these, circumbenzene (coronene) [4][5][6][7][8] and circumnaphthalene (ovalene) 9 (Figure 1a) stand as the smallest circumarenes, synthesized by Scholl and Clar, respectively, in the 20th century. Subsequently, their soluble derivatives were later employed in supramolecular self-assembly and electronic device applications.…”

Section: Introductionmentioning

confidence: 99%

Towards the Tetrabenzo-Fused Circumazulene via In-Solution and On-Surface Synthesis

Wu,

Xu,

et al. 2024

Organic Materials

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The synthesis of circumazulene, a nonalternant isomer of circumnaphthalene, and its π-expanded derivatives poses a considerable challenge due to the lack of a suitable synthetic strategy. In this work, we present our efforts toward achieving tetrabenzo-fused circumazulene (1) through both solution and on-surface syntheses. In the case of in-solution synthesis, we obtained a product (P) with the desired target mass, but the structural verification proved to be challenging owing to the presence of various structural isomers. In the on-surface synthesis approach, a series of unexpected azulene-embedded nanographene were obtained, including a molecule with an additional pentagonal ring (U1) based on the backbone of 1. Furthermore, theoretical calculations were conducted to shed light on these unexpected structures and to investigate their aromaticity. This work opens a new avenue for the design and synthesis of novel nonalternant graphene nanostructures incorporating circumarene.

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Maßgeschneiderte Synthese von Graphennanostrukturen mit Zickzack‐Rändern

Cited by 51 publications

References 175 publications

Circumcoronenes

Circumcoronenes

Benzo‐Fused Perylene Oligomers with up to 13 Linearly Annulated Rings

Towards the Tetrabenzo-Fused Circumazulene via In-Solution and On-Surface Synthesis

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