Chirality Transfer from Single Molecules into Self‐Assembled Monolayers

Fasel, Román; Parschau, Man Fred; Ernst, Karl‐Heinz

doi:10.1002/anie.200352232

Cited by 202 publications

(189 citation statements)

References 37 publications

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“…20b and c. The Menantiomer shows the corresponding mirror structures, i.e., with opposite handedness (not shown) [122]. XPD revealed that three rings on the proximal end are aligned parallel to the surface plane [35], and force-field calculations for the saturation structure provided a model in good agreement with the observations (Fig.…”

Section: Racemic Mixturessupporting

confidence: 60%

“…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]. This aromatic hydrocarbon is basically a construct of seven orthoannulated C6 rings and therefore an example of a chiral molecule without a stereogenic center (Fig.…”

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 Mixturessupporting

confidence: 60%

Section: Racemic Mixturesmentioning

confidence: 99%

Molecular chirality at surfaces

Ernst

2012

Physica Status Solidi (b)

Self Cite

221

264

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“…54−56 In that case, the chirality of the molecule is transferred to the molecular assembly. 57 Chiral structure can also be achieved using achiral molecules. 1,54,55,58,59 In that case, the chirality results from the specific arrangement of the molecules.…”

Section: ■ Introductionmentioning

confidence: 99%

Coexisting Chiral Two-Dimensional Self-Assembled Structures of 1,2,3,4-Tetrahydronaphthalene Molecules: Porous Pinwheel Nanoarchitecture and Close-Packed Herringbone Arrangement

2017

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International audienceThe self-assembly of 1,2,3,4-tetrahydronaph-thalene molecules is investigated using scanning tunneling microscopy (STM) at the solid/liquid interface. STM reveals that the molecule self-assembles into a chiral close-packed herringbone structure and a chiral porous pinwheel nano-architecture at room temperature on graphite. The two networks are equally distributed on the surface, and the two enantiomeric molecular arrangements of the two structures are observed. Variation of the molecule−surface epitaxial relationship suggests that the pinwheel arrangement favors molecule− surface interactions, whereas the herringbone arrangement favors intermolecular interactions

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“…1c. [10] Similar to the frustrated lattice structures observed for crystalline polymers of single helicity, e.g . isotactic poly(propylene), [12] not all helices can be aligned 'in phase'.…”

Section: Transfer Of Handedness From Single Molecules Into 2d Crystalsmentioning

confidence: 55%

“…One example are the pure [7]H enantiomers on Cu(111). [10] Close to monolayer saturation, handed pinwheel structures are observed via STM (Fig 1a,b). The ( M )- [7]H-pinwheels have the opposite handedness to the ( P )- [7] H-pinwheels.…”

Section: Transfer Of Handedness From Single Molecules Into 2d Crystalsmentioning

confidence: 87%

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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Chirality Transfer from Single Molecules into Self‐Assembled Monolayers

Cited by 202 publications

References 37 publications

Molecular chirality at surfaces

Molecular chirality at surfaces

Coexisting Chiral Two-Dimensional Self-Assembled Structures of 1,2,3,4-Tetrahydronaphthalene Molecules: Porous Pinwheel Nanoarchitecture and Close-Packed Herringbone Arrangement

Expression and Amplification of Chirality in Two-Dimensional Molecular Crystals

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