Homochiral Conglomerates and Racemic Crystals in Two Dimensions: Tartaric Acid on Cu(110)

Romer, Sara; Behzadi, Bahar; Fasel, Román; Ernst, Karl‐Heinz

doi:10.1002/chem.200400962

Cited by 77 publications

(98 citation statements)

References 35 publications

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“…The adsorption of the racemate reveals in LEED a superposition of (1 2, À8 2) and (1-2, 8 2) patterns ( Fig. 18a and b) [119]. This is a strong indication of conglomerate formation, whereby the electron beam probes both homochiral domains.…”

Section: Racemic Mixturesmentioning

confidence: 89%

“…Further support for this scenario comes from the fact that the saturation coverage for the pure enantiomers is higher. A formation of the enantiomorphous (4-1, 2 4) phase is not observed for the racemic mixture, which saturates in a c(2 Â 4) structure [119]. Other than tartaric acid, racemic heptahelicene ( [7]H; C 30 H 18 ) forms completely different structures from the pure enantiomers on Cu(111) [122][123][124][125].…”

Section: Racemic Mixturesmentioning

confidence: 99%

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Molecular chirality at surfaces

Ernst

2012

Physica Status Solidi (b)

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With the adsorption of larger molecules being increasingly tackled by surface scientists, the aspect of chirality often plays a role. This paper gives a topical review of molecular chirality at surfaces and gives a phenomenological overview of different aspects of adsorption and self‐assembly of chiral and prochiral molecules and the principles of mirror‐symmetry breaking at a surface. After a brief introduction into the history of molecular chirality and the important role it played for understanding the spatial structure of molecules, definitions of chirality are presented. Topics treated here are principle ways to create single chiral adsorbates, chiral ensembles, and monolayers by achiral molecules, adsorption of intrinsically chiral molecules at achiral and chiral surfaces, long‐range symmetry breaking in two‐dimensional (2D) crystals due to additional chiral bias, chiral restructuring of solid surfaces under the influence of chiral molecules, switching the handedness of adsorbates, and chirality at the liquid/air interface. An outlook onto further potential research directions and recommendations for further reading, including nonsurface‐related sources of chiral topics completes this paper.

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Section: Racemic Mixturesmentioning

confidence: 89%

Section: Racemic Mixturesmentioning

confidence: 99%

Molecular chirality at surfaces

Ernst

2012

Physica Status Solidi (b)

Self Cite

223

264

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“…For racemic TA, on the other hand, a 2D conglomerate is observed only for the bitartrate species, where homochiral (9 0, 1 2) and (9 0, -1 2) domains coexist on the surface. [16] The corresponding LEED pattern shows a superposition of both structures (Fig. 3).…”

Section: Racemic Crystals Versus Conglomeratesmentioning

confidence: 94%

“…This has been shown for racemic tartaric acid (TA) on Cu(110). [16] Depending on temperature and/or coverage, TA forms different lattice structures on the surface. [17] In particular, if one or both carboxylate groups react with the copper surface, bitartrate or monotartrate species will be present, respectively.…”

Section: Racemic Crystals Versus Conglomeratesmentioning

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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“…20 To date, just two instances of adsorption of tartaric acid from a racemic mixture have been reported in the literature. 22,23 Low energy electron diffraction (LEED) results indicate that domain organization on Cu(110) is highly coverage dependent: at low coverages, the films separate into enantiomorphous domains of bitartrate species, and at higher coverages a racemic lattice that is composed of monotartrate adsorbates is proposed. 23 This separation of enantiomers into homochiral bitartrate domains upon adsorption of racemic tartaric acid onto Cu(110) at low coverage was confirmed recently with scanning tunneling microscopy.…”

Section: Introductionmentioning

confidence: 99%

Chiral Steering of Molecular Organization in the Limit of Weak Adsorbate−Substrate Interactions: Enantiopure and Racemic Tartaric Acid Domains on Ag(111)

et al. 2010

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The influence of intermolecular interactions involving molecular chiral centers on two-dimensional organization in the limit of a weak adsorbate-surface interaction has been studied with low-temperature scanning tunneling microscopy (STM) and density functional theory (DFT). A model system composed of a chiral organic molecule, tartaric acid, and an inert metallic surface, Ag(111), was employed. Dual component films formed from the serial deposition of (S,S)-and (R,R)-tartaric acid enantiomers onto this surface exhibit homochiral domain formation as revealed by molecularly resolved STM images. In contrast, a unique tartaric acid enantiomeric heteropair is experimentally and computationally verified as the basis unit of films formed via the deposition of both enantiomers simultaneously from a racemic (1:1) mixture. The molecular adsorption geometry relative to the Ag(111) lattice in both enantiomerically pure and racemic domains is determined primarily by the interaction of chiral centers between nearest neighbors.

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Homochiral Conglomerates and Racemic Crystals in Two Dimensions: Tartaric Acid on Cu(110)

Cited by 77 publications

References 35 publications

Molecular chirality at surfaces

Molecular chirality at surfaces

Expression and Amplification of Chirality in Two-Dimensional Molecular Crystals

Chiral Steering of Molecular Organization in the Limit of Weak Adsorbate−Substrate Interactions: Enantiopure and Racemic Tartaric Acid Domains on Ag(111)

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