Corannulenecarbaldehyde: High‐­Yielding Synthesis by Rieche Form­ylation and Facile Access to a Variety of Corannulene Derivatives

Rajeshkumar, Venkatachalam; Lee, Yuan Theng; Stuparu, Mihaiela C.

doi:10.1002/ejoc.201501226

Cited by 26 publications

(24 citation statements)

References 28 publications

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“…[10,11] During the last decades the chemistry andp hysics of CA-derived buckybowl derivatives was thoroughlys tudied. [12][13][14][15][16][17][18] However,c omparably less work has been carried out in the field of Idpc and its derivatives.T he first synthetic approach towards Idpc by palladium catalyzed cyclization of suitable precursors was reported already in 2000, but lacked generality. [19] The aluminium-oxide mediated cove-regionr ing-closure through CÀF bond activation of fluoroarenes [20] towards pristine Idpc and other bowl-shaped PAHs developed by Amsharov et al in 2012 constituted am ajor breakthrough.…”

Section: Introductionmentioning

confidence: 99%

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Geodesic‐Planar Conjugates: Substituted Buckybowls—Synthesis, Photoluminescence and Electrochemistry

Bayer

Herberger

Holz

et al. 2020

Chemistry A European J

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CÀCc ross coupling products of bowl-shaped asindaceno[3,2,1,8,7,6-pqrstuv]picene (Idpc) and different planar arenes and ethynyl-arenes were synthesized. Photoluminescence as well as electrochemical properties of all products were investigated and complemented by time-dependent quantum chemical calculations. UV/Vis spectroelectro-chemistry investigations of the directly linked (Idpc) 2 indicated the absence of anyi ntramolecular charge-transfer transition of intermittently formed (Idpc) 2 C À .A ll coupling products showed fluorescence. Ferrocene-1-yl-Idpc was structurally characterized by X-ray diffraction and is ar are example of a ferrocene-containingb uckybowl exhibiting luminescence.

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Section: Introductionmentioning

confidence: 99%

“…During the last decades the chemistry and physics of CA‐derived buckybowl derivatives was thoroughly studied [12–18] . However, comparably less work has been carried out in the field of Idpc and its derivatives.…”

Section: Introductionmentioning

confidence: 99%

Geodesic‐Planar Conjugates: Substituted Buckybowls—Synthesis, Photoluminescence and Electrochemistry

Bayer

Herberger

Holz

et al. 2020

Chemistry A European J

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“…The synthesis of corannulene carbaldehyde 102 at a 15 g scale and in an isolated yield of >90% made it possible to explore its application in synthesis of corannulenebased vinylenes 103 through a Wittig olefination reaction with a variety of commercially available phosphonium ylides (Fig. 9a) 61,62 . In subsequent studies, these stilbene-like precursors were shown to undergo a photocyclisation-induced oxidation reaction to yield extended corannulenes 104 62,63 .…”

Section: Photochemistrymentioning

confidence: 99%

Synthesis of corannulene-based nanographenes

2019

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Corannulene (C 20 H 10) is a polycyclic hydrocarbon in which five six-membered rings surround a central five-membered ring to construct a bowl-like aromatic structure. Here we examine the development of synthetic strategies that allow for the growth of the peripheral aromatic rings as a means to extend the aromatic area of the central corannulene nucleus and provide access to unique nanocarbon molecules. s p 2-hybridised structures of carbon have fascinated the research community for a very long time. In 1985, buckminsterfullerene, otherwise known as C 60 , was discovered (Fig. 1a) 1. In this ball-shaped molecule, the curvature in the structure stems from the presence of fivemembered rings. In 1991, carbon nanotubes arrived on the scene 2. Here, the structure is cylindrical and composed of only rolled-up six-membered rings. In 2004, a sheet-like single layer from graphite-graphene-was isolated 3. All of these materials were shown to have extraordinary electronic and mechanical properties due to their unique curved or planar sp 2-hybridised aromatic structures. Inspired by these discoveries, chemists have been developing strategies to access such aromatic hydrocarbons through rational ('bottom-up') synthetic approaches. Scott's 12-step chemical synthesis of fullerene C 60 from a rationally designed precursor is a testament to the ingenuity and resourcefulness of organic chemists 4. In planar structures, nanographenes (well-defined cutouts of graphene with nano-scale dimensions) can now be prepared on a regular basis with a very diverse portfolio 5. It is expected that combining the planar structure of graphene with the curvature of fullerenes may produce hybrid materials with interesting properties 6-8. To induce non-planarity into nanographenes, a practical approach would be to introduce a fivemembered ring such as in the case of fullerene, C 60. A perfect building block that allows for such a structural arrangement to happen is corannulene (1)-a molecule in which five six-membered rings surround a central five-membered ring to give a bowl-like structure (Fig. 1b) 9-20. Corannulene also offers many beneficial features as a molecular building block. It has high solubility in common organic solvents. It can be derivatized in a well-defined manner. Due to synthetic ease, the derivatives can be prepared on a multigram scale. These attributes are important as they allow for the scalable preparation of carefully designed corannulene-based building blocks and the subsequent synthesis, purification and structural analysis of the larger (fused) aromatic systems. Recently, therefore, there has been a surge in employment of corannulene as a core molecule in the synthesis of extended aromatic structures. Our aim in this review article is to discuss

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“…To a round-bottomed ask cooled to 0 C containing MWCNTs (1.00 g) and dichloromethyl methyl ether (1.5 mL) in anhydrous CH 2 Cl 2 (50 mL), TiCl 4 (1 mL) was added dropwise under N 2 , and the mixture, under the above conditions, was magnetically stirred for 1 h. 42 The stirring was continued at room temperature for 20 h. The product was ltered off. MWCNT-CHO precursor was washed with water (100 mL) and acetone (50 mL) until a colourless ltrate was observed.…”

Section: Rieche Formylation Of Mwcntsmentioning

confidence: 99%

Rieche formylation of carbon nanotubes – one-step and versatile functionalization route

Kolanowska

Kuziel

et al. 2017

RSC Adv.

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Corannulenecarbaldehyde: High‐Yielding Synthesis by Rieche Formylation and Facile Access to a Variety of Corannulene Derivatives

Cited by 26 publications

References 28 publications

Geodesic‐Planar Conjugates: Substituted Buckybowls—Synthesis, Photoluminescence and Electrochemistry

Geodesic‐Planar Conjugates: Substituted Buckybowls—Synthesis, Photoluminescence and Electrochemistry

Synthesis of corannulene-based nanographenes

Rieche formylation of carbon nanotubes – one-step and versatile functionalization route

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Corannulenecarbaldehyde: High‐­Yielding Synthesis by Rieche Form­ylation and Facile Access to a Variety of Corannulene Derivatives

Cited by 26 publications

References 28 publications

Geodesic‐Planar Conjugates: Substituted Buckybowls—Synthesis, Photoluminescence and Electrochemistry

Geodesic‐Planar Conjugates: Substituted Buckybowls—Synthesis, Photoluminescence and Electrochemistry

Synthesis of corannulene-based nanographenes

Rieche formylation of carbon nanotubes – one-step and versatile functionalization route

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Product

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Corannulenecarbaldehyde: High‐Yielding Synthesis by Rieche Formylation and Facile Access to a Variety of Corannulene Derivatives