Quadrannulene: A Nonclassical Fullerene Fragment

Bharat,; Bhola, Radha; Bally, Thomas; Valente, Alessandro; Cyrański, Michał K.; Dobrzycki, Łukasz; Spain, Stephen M.; Rempała, Paweł; Chin, Matthew R.; King, Benjamin T.

doi:10.1002/anie.200905633

Cited by 104 publications

(74 citation statements)

References 30 publications

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“…The shapes of these circulenes change from a bowl ([5]circulene) through a plane ([6]circulene) to a saddle ([7]circulene). Although investigations of [4]circulene remain theoretical, tetrabenzo[4]circulene has recently been synthesized and determined to be a bowl‐shaped molecule 5. [8]Circulene ( 1 ) has not yet been synthesized in the laboratory, presumably because of its highly strained structure and instability.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Structural Analysis, and Properties of [8]Circulenes

2013

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Polygons: [8]Circulenes were easily prepared by Pd-catalyzed annulations of tetraiodotetraphenylenes with alkynes. Their saddle-shaped structure with an [8]radialene character was identified by X-ray crystallography. Similar to 1,3,5,7-cyclooctatetraene, they have a tub-shaped eight-membered ring, but all of the bond lengths and bond angles are almost equal. Variable-temperature NMR investigations showed interesting dynamic behavior.

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Section: Methodsmentioning

confidence: 99%

Synthesis, Structural Analysis, and Properties of [8]Circulenes

2013

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“…[n]Circulene is a macrocyclic arene in which a central n-sided polygon is completely surrounded and fused by benzenoids. [1] Only three members of this family, [5]circulene (or corannulene), [2] [6]circulene (or coronene), [3] and [7]circulene (or pleiadannulene) [4] have been prepared to date. The shapes of these circulenes change from a bowl ( [5]circulene) through a plane ( [6]circulene) to a saddle ( [7]circulene).…”

mentioning

confidence: 99%

“…[1] Only three members of this family, [5]circulene (or corannulene), [2] [6]circulene (or coronene), [3] and [7]circulene (or pleiadannulene) [4] have been prepared to date. The shapes of these circulenes change from a bowl ( [5]circulene) through a plane ( [6]circulene) to a saddle ( [7]circulene). Although investigations of [4]circulene remain theoretical, tetrabenzo [4]circulene has recently been synthesized and determined to be a bowl-shaped molecule.…”

mentioning

confidence: 99%

“…Although investigations of [4]circulene remain theoretical, tetrabenzo [4]circulene has recently been synthesized and determined to be a bowl-shaped molecule. [5] [8]Circulene (1) has not yet been synthesized in the laboratory, presumably because of its highly strained structure and instability. In contrast, its various planar analogues, such as tetraoxo [8]circulene, [6] octathio [8]circulene, [7] and tetracyclopenta[def,jkl,pqr,vwx]tetraphenylene (TCT), [8] have been successfully generated.…”

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Synthesis, Structural Analysis, and Properties of [8]Circulenes

Feng

Kuo

2013

Angewandte Chemie

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Polygone: [8]Circulene wurden durch Pd‐katalysierte Anellierungen von Tetraiodtetraphenylenen mit Alkinen hergestellt. Ihre sattelförmige Struktur mit [8]Radialen‐Charakter wurde durch Kristallstrukturanalyse identifiziert. Sie haben, ähnlich wie 1,3,5,7‐Cyclooctatetraene, einen wannenförmigen achtgliedrigen Ring, die Bindungslängen und ‐winkel sind jedoch alle nahezu gleich. Temperaturabhängige NMR‐Messungen zeigten ein ungewöhnliches dynamisches Verhalten.

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“…[2] Curvature or contortion can be implemented into PAHs by the introduction of cove or fjord regions, even if the PAHs are consisting of six-membered rings exclusively. [1d, 3] Another possibility is the embedding of rings that are deviating in size from the six-membered one, such as four-, [4] five-, [5] seven-, [5f, 6] or eight-membered rings to cause contortion. [6b, 7] With the exception of the four-membered ring containing PAH, the latter are by far the most rare ones.…”

Section: A Chiral Polycyclic Aromatic Hydrocarbon Monkey Saddlementioning

confidence: 99%

A Chiral Polycyclic Aromatic Hydrocarbon Monkey Saddle

2019

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A contorted polycyclic aromatic hydrocarbon (PAH) in the shape of a monkey saddle has been synthesized in three steps from a readily available truxene precursor. The monkey saddle PAH is consisting of three five‐, seven six‐, and three eight‐membered rings and has been unambiguously characterized by single‐crystal X‐ray diffraction. Owing to the three biaryl axes the monkey saddle PAH is inherently chiral. The inversion of the two enantiomeric structures into each other preferably occurs through a twisting of peripheral rings rather than by a fully planar intermediate, as has been calculated by DFT methods. Enantiomers were separated by chiral HPLC and inversion barriers determined by variable temperature circular dichroism spectroscopy, supporting the twisting mechanism.

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Quadrannulene: A Nonclassical Fullerene Fragment

Cited by 104 publications

References 30 publications

Synthesis, Structural Analysis, and Properties of [8]Circulenes

Synthesis, Structural Analysis, and Properties of [8]Circulenes

Synthesis, Structural Analysis, and Properties of [8]Circulenes

A Chiral Polycyclic Aromatic Hydrocarbon Monkey Saddle

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