Buckybowls on Metal Surfaces: Symmetry Mismatch and Enantiomorphism of Corannulene on Cu(110)

Parschau, Manfred; Fasel, Román; Ernst, Karl‐Heinz; Gröning, Oliver; Brandenberger, Louis; Schillinger, R.; Greber, Thomas; Seitsonen, Ari P.; Wu, Yao Ting; Siegel, Jay S.

doi:10.1002/anie.200700610

Cited by 85 publications

(105 citation statements)

References 38 publications

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“…When unsubstituted corannulene is adsorbed onto Cu(110), a strong interaction with the surface leads to the formation of a quasihexagonal packing with weak direct intermolecular interactions. [18] This has prompted us to prepare the penta-tert-butyl derivative of corannulene that bears bulky groups on all five double bonds of the rim. [19] These groups raise the height of the central polyaromatic core and therefore reduce its interaction with Ag(111), which has a lower surface energy and shows a much weaker molecule-substrate interaction than Cu(110).…”

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confidence: 99%

Bicomponent Supramolecular Packing in Flexible Phthalocyanine Networks

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confidence: 99%

Bicomponent Supramolecular Packing in Flexible Phthalocyanine Networks

et al. 2008

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“…In highly resolved STM images corannulene appears as doughnut, and comparison with results from semi-empirical extended Hückel calculations strongly favors an adsorption geometry in which the bowl opening points away from the surface. X-ray photoelectron diffraction (XPD) measurements additionally revealed a small tilt of the C 5 -rotational axis away from the surface normal (Parschau et al 2007). Such adsorption geometry suggests, that the chemical bond between molecule and copper surface is formed via single a C-C bond (η 2 ) of the pentagonal ring and a copper surface atom.…”

Section: Adsorption-induced Chiralitymentioning

confidence: 98%

“…The 'buckybowl' corannulene, for example, forms spontaneously mirror domains on Cu(110) (Parschau et al 2007). The bowl-shaped fullerene fragment molecule has C 5 v symmetry.…”

Section: Adsorption-induced Chiralitymentioning

confidence: 99%

Amplification of Chirality at Solid Surfaces

Ernst

2009

Orig Life Evol Biosph

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Symmetry-breaking phenomena in two-dimensional crystallization at surfaces are reviewed and the potential impact to chiral amplification in three-dimensional systems in connection with the origin of homochirality in the biomolecular world is discussed. Adsorption of prochiral molecules leads to two-dimensional conglomerates, i.e., on a local scale spontaneously to homochiral crystal structures. Small enantiomeric excess or chiral impurities in this environment install homochirality on a global scale, that is, on the entire surface.

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“…[9,20] For ( R , R )-and ( S , S )-bitartrate a zigzag distortion was determined experimentally. [21] Density functional theory (DFT) calculations, however, also predict a chiral zigzag conformation after deprotonation of both carboxyl groups for achiral ( R , S )-TA ( meso-tartaric acid) and succinic acid (SU) on Cu(110).…”

Section: Adsorption-induced Chiralitymentioning

confidence: 99%

Expression and Amplification of Chirality in Two-Dimensional Molecular Crystals

Ernst¹

2008

Chimia

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Expression and amplification of chirality in two-dimensional molecular crystals Expression and amplification of chirality in two-dimensional molecular crystals Abstract Chirality can be bestowed onto achiral surfaces by adsorption of chiral molecules. This offers a good opportunity to study two-dimensional chiral crystallization phenomena, like lateral resolution of enantiomers or the transfer of handedness from single molecules into mesoscopic ensembles with high resolution by scanning probe microscopy. Induction of homochirality on surfaces via cooperatively amplified interactions in molecular monolayers is a new phenomenon of supramolecular surface chirality. Prochiral molecules will turn into either handedness upon adsorption, but doping with intrinsically chiral molecules breaks this symmetry and induces homochirality. A similar effect is induced by a small enantiomeric excess. The excess molecules provide the chiral bias that becomes amplified into single lattice chirality. Expression and Amplification of Chirality in Tw o-Dimensional Molecular CrystalsKarl-Heinz Ernst * Dedicated to Professor Jack D. Dunitz on the occasion of his 85 th birthdayAbstract: Chirality can be bestowed onto achiral surfaces by adsorption of chiral molecules. This offers a good opportunity to study two-dimensional chiral crystallization phenomena, like lateral resolution of enantiomers or the transfer of handedness from single molecules into mesoscopic ensembles with high resolution by scanning probe microscopy. Induction of homochirality on surfaces via cooperatively amplified interactions in molecular monolayers is a new phenomenon of supramolecular surface chirality. Prochiral molecules will turn into either handedness upon adsorption, but doping with intrinsically chiral molecules breaks this symmetry and induces homochirality. A similar effect is induced by a small enantiomeric excess. The excess molecules provide the chiral bias that becomes amplified into single lattice chirality.

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Buckybowls on Metal Surfaces: Symmetry Mismatch and Enantiomorphism of Corannulene on Cu(110)

Abstract: Fivefold versus twofold: Symmetry‐breaking interactions in the monolayer of the buckybowl corannulene on Cu(110) lead to the formation of extended mirror domains (see picture). The molecules are adsorbed in a tilted geometry with the bowl opening pointing away from the surface.

Cited by 85 publications

References 38 publications

Bicomponent Supramolecular Packing in Flexible Phthalocyanine Networks

Bicomponent Supramolecular Packing in Flexible Phthalocyanine Networks

Amplification of Chirality at Solid Surfaces

Expression and Amplification of Chirality in Two-Dimensional Molecular Crystals

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