Flattening of a Curved-Surface Buckybowl (Corannulene) by η<sup>6</sup> Coordination to {Cp*Ru}<sup>+</sup>

Vecchi, Paul A.; Martín‐Alvarez, José M.; Ellern, Arkady; Angelici, Robert J.; Syguła, Andrzej; Sygula, Renata; Rabideau, Peter W.

doi:10.1021/om0505458

Cited by 67 publications

(65 citation statements)

References 42 publications

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“…0.87 Å in corannulene (88)). With the exception of a metal complex, [70] this is the flattest corannulene system ever generated. The Itami-Scott collaboration then went one better by subjecting 90 to an intramolecular Scholl reaction that delivered a "grossly warped nanographene" 92 in 62% yield (Scheme 22).…”

Section: Arylation Reactionsmentioning

confidence: 99%

Extraordinary Transformations to Achieve the Synthesis of Remarkable Aromatic Compounds

Bodwell

2014

The Chemical Record

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Note from the Editor: When we walk around a sculpture, it can speak to us in many ways, sometimes quite differently from various view points. Central to Tetsuo Nozoe and the Nozoe Autograph Book project are novel aromatic compounds. Just look at nearly any page and such compounds jump out at us. We can categorize them in many ways. Their structures. Their physical properties. Their pharmacological and toxicological properties. Their commercial utilities. Their symmetry. Their size. In this essay, Graham Bodwell brings to us his analysis of the various ways in which some of the most remarkable of these compounds have been ingeniously synthesized. We are privileged to have Bodwell's vision and his sense of organization and beauty. Tetsuo Nozoe would have beamed! —Jeffrey I. Seeman Guest Editor University of Richmond Richmond, Virginia 23173, USA E‐mail: jseeman@richmond.edu

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Section: Arylation Reactionsmentioning

confidence: 99%

Extraordinary Transformations to Achieve the Synthesis of Remarkable Aromatic Compounds

Bodwell

2014

The Chemical Record

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“…Fullerene and CNT and their derivatives form a coordination complex with various metal ion through their π-surfaces to form exo-as well as endo-hedral complexes, which have been used as a potential material in various fields such as molecular electronics and magnetic resonance imaging studies [100][101][102]. Interestingly, π-curved conjugated fragment 1 (bowl depth = 0.87 Å) preferentially coordinates with various metal ions in the convex surface in the η 1 , η 2 , and η 6 modes [23,31,32,39,[103][104][105][106]. Some corannulene derivatives form concave as well as convex face η 6 -coordination complexes with ruthenium(II) [31,39,104].…”

Section: Chiral Metal Complexes Of Buckybowlsmentioning

confidence: 99%

“…Interestingly, π-curved conjugated fragment 1 (bowl depth = 0.87 Å) preferentially coordinates with various metal ions in the convex surface in the η 1 , η 2 , and η 6 modes [23,31,32,39,[103][104][105][106]. Some corannulene derivatives form concave as well as convex face η 6 -coordination complexes with ruthenium(II) [31,39,104]. Similarly, another C 3v symmetric, Symmetry 2017, 9, 174 15 of 25 curved π-conjugated bowl, 2, forms coordination complexes through the η 1 , η 2 , η 4 , η 5 , and η 6 modes with limited transition metal ions [107].…”

Section: Chiral Metal Complexes Of Buckybowlsmentioning

confidence: 99%

Chiral Buckybowl Molecules

Kanagaraj

Lin

et al. 2017

Symmetry

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Buckybowls are polynuclear aromatic hydrocarbons that have a curved aromatic surface and are considered fragments of buckminsterfullerenes. The curved aromatic surface led to the loss of planar symmetry of the normal aromatic plane and may cause unique inherent chirality, so-called bowl chirality, which it is possible to thermally racemize through a bowl-to-bowl inversion process. In this short review, we summarize the studies concerning the special field of bowl chirality, focusing on recent practical aspects of attaining diastereo/enantioenriched chiral buckybowls through asymmetric synthesis, chiral optical resolution, selective chiral metal complexation, and chiral assembly formation.

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“…Quite recently we also succeeded in X-ray structure determination of the monometallated complex of 1 with (Cp*Ru) þ [64]. As in the bis-ruthenium analog the metal was h 6 coordinated to one of the benzene rings of 1 on its exo (convex) face.…”

Section: Transition Metal Complexesmentioning

confidence: 99%

“…This is the first experimental evidence demonstrating the exo preference of h 6 coordination of (Cp*Ru) þ to corannulene. Also, another bis-metallated complex, [(Cp*Ru) 2 (m 2 -h 6 ,h 6 -C 20 H 10 )][SbF 6 ] 2 was prepared and characterized by X-ray [64].…”

Section: Transition Metal Complexesmentioning

confidence: 99%

Synthesis and Chemistry of Polycyclic Aromatic Hydrocarbons with Curved Surfaces: Buckybowls

Syguła

Rabideau

2006

Carbon‐Rich Compounds

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Flattening of a Curved-Surface Buckybowl (Corannulene) by η⁶ Coordination to {Cp*Ru}⁺

Cited by 67 publications

References 42 publications

Extraordinary Transformations to Achieve the Synthesis of Remarkable Aromatic Compounds

Extraordinary Transformations to Achieve the Synthesis of Remarkable Aromatic Compounds

Chiral Buckybowl Molecules

Synthesis and Chemistry of Polycyclic Aromatic Hydrocarbons with Curved Surfaces: Buckybowls

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Flattening of a Curved-Surface Buckybowl (Corannulene) by η6 Coordination to {Cp*Ru}+

Cited by 67 publications

References 42 publications

Extraordinary Transformations to Achieve the Synthesis of Remarkable Aromatic Compounds

Extraordinary Transformations to Achieve the Synthesis of Remarkable Aromatic Compounds

Chiral Buckybowl Molecules

Synthesis and Chemistry of Polycyclic Aromatic Hydrocarbons with Curved Surfaces: Buckybowls

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Product

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Flattening of a Curved-Surface Buckybowl (Corannulene) by η⁶ Coordination to {Cp*Ru}⁺