A helically twisted ribbon-shaped nanographene constructed around a fenestrindane core

Sun, Xiao-Qing; Wong, Wai-Shing; Li, Yuke; Kuck, Dietmar; Chow, Hak‐Fun

doi:10.1039/d1qo00929j

Cited by 7 publications

(3 citation statements)

References 49 publications

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“…By this means, the helicity of flexible ribbons can be biased, which is a facile alternative compared to the separation of atropo-enantiomers formed statistically during the annulation of achiral building blocks. Nevertheless, the latter approach is still the method of choice for laterally extended and more rigid nanoribbons whose edge functionalization defines whether stereoisomers can be isolated or not. − Thus, a variety of new molecular materials with a high chiroptical response have been realized, cumulating in the design of a supertwistacene by the Wang group in 2020, proving GNRs as a considerable alternative for pristine carbo[ n ]helicene backbones. − …”

Section: Introductionmentioning

confidence: 99%

Helically Twisted Nanoribbons Based on Emissive Near-Infrared Responsive Quaterrylene Bisimides

et al. 2022

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Graphene nanoribbons (GNRs) have the potential for next-generation functional devices. So far, GNRs with defined stereochemistry are rarely reported in literature and their optical response is usually bound to the ultraviolet or visible spectral region, while covering the near-infrared (NIR) regime is still challenging. Herein, we report two novel quaterrylene bisimides with either one-or twofold-twisted π-backbones enabled by the steric congestion of a fourfold bay arylation leading to an end-toend twist of up to 76°. The strong interlocking effect of the πstacked aryl substituents introduces a rigidification of the chromophore unambiguously proven by single-crystal X-ray analysis. This leads to unexpectedly strong NIR emissions at 862 and 903 nm with quantum yields of 1.5 and 0.9%, respectively, further ensuring high solubility as well as resolvable and highly stable atropo-enantiomers. Circular dichroism spectroscopy of these enantiopure chiral compounds reveals a strong Cotton effect Δε of up to 67 M −1 cm −1 centered far in the NIR region at 849 nm.

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Section: Introductionmentioning

confidence: 99%

Helically Twisted Nanoribbons Based on Emissive Near-Infrared Responsive Quaterrylene Bisimides

et al. 2022

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“…In the recent years, significant efforts have been expended towards synthesizing fenestrane-based nanographenes. 21,49,50 We hope that these findings will stimulate further experimental efforts in synthesizing THFS-carbon from [4.6.4.6]fenestrane, thus expanding the carbon family for practical applications.…”

Section: Discussionmentioning

confidence: 98%

THFS-carbon: a theoretical prediction of metallic carbon allotrope with half-auxeticity, planar tetracoordinate carbon, and potential application as anode for sodium-ion batteries

Meng

et al. 2023

Phys. Chem. Chem. Phys.

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“…However, this arenium cation mechanism begins with ipso protonation on the methoxylated carbon atom, which has a positive Mulliken charge density and thus is unlikely protonated. To further expand the π-backbone, 195 was synthesized in a yield of 11% by oxidation of the tetra(biphenyl) tetrabenzofenestrane precursor with DDQ/CF 3 SO 3 H at 0 °C with formation of 10 C–C bonds . X-ray crystallography reveals that 195 is helically twisted with D 2 symmetry and a pair of antipodal enantiomers of 195 aggregates in the solid state.…”

Section: Synthesis Of Curved Polycyclic Aromatics Through Scholl Reac...mentioning

confidence: 99%

The Scholl Reaction as a Powerful Tool for Synthesis of Curved Polycyclic Aromatics

2022

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The past decade has witnessed remarkable success in the synthesis of curved polycyclic aromatics through Scholl reactions which enable oxidative aryl–aryl coupling even in company with the introduction of significant steric strain. These curved polycyclic aromatics are not only unique objects of structural organic chemistry in relation to the nature of aromaticity but also play an important role in bottom-up approaches to precise synthesis of nanocarbons of unique topology. Moreover, they have received considerable attention in the fields of supramolecular chemistry and organic functional materials because of their interesting properties and promising applications. Despite the great success of Scholl reactions in synthesis of curved polycyclic aromatics, the outcome of a newly designed substrate in the Scholl reaction still cannot be predicted in a generic and precise manner largely due to limited understanding on the reaction mechanism and possible rearrangement processes. This review provides an overview of Scholl reactions with a focus on their applications in synthesis of curved polycyclic aromatics with interesting structures and properties and aims to shed light on the key factors that affect Scholl reactions in synthesizing sterically strained polycyclic aromatics.

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A helically twisted ribbon-shaped nanographene constructed around a fenestrindane core

Abstract: A helically twisted ribbon-shaped nanographene 3 containing four pentagons, eighteen hexagons and four heptagons was synthesized by a cascade of classical Scholl and non-classical Scholl-type cycloheptatriene formation reactions. In the...

Cited by 7 publications

References 49 publications

Helically Twisted Nanoribbons Based on Emissive Near-Infrared Responsive Quaterrylene Bisimides

Helically Twisted Nanoribbons Based on Emissive Near-Infrared Responsive Quaterrylene Bisimides

THFS-carbon: a theoretical prediction of metallic carbon allotrope with half-auxeticity, planar tetracoordinate carbon, and potential application as anode for sodium-ion batteries

The Scholl Reaction as a Powerful Tool for Synthesis of Curved Polycyclic Aromatics

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