Induction of Homochirality in Achiral Enantiomorphous Monolayers

Parschau, Manfred; Romer, Sara; Ernst, Karl‐Heinz

doi:10.1021/ja044136z

Cited by 166 publications

(145 citation statements)

References 30 publications

(33 reference statements)

Supporting

Mentioning

136

Contrasting

Unclassified

Order By: Relevance

“…This kind of amplification of chirality is quite similar to the "sergeants-and-soldiers" principle, first reported for helical polymers with chiral side chains in solution [31]. In two dimensions this phenomenon has been first observed by us for racemic monolayers of prochiral succinic and meso-tartaric acid after doping with intrinsically chiral (R,R)-or (S,S)-tartaric acid [32][33][34]. The corresponding amplification of chirality in helical copolymers with small enantiomeric excess in the side chains has been coined as "majority rule" [35], and the 2-D analogue has been reported recently [36].…”

Section: Helical Aromatessupporting

confidence: 76%

Intermediate structures in two-dimensional molecular self-assembly

Ernst

2010

Front. Phys. China

Self Cite

View full text Add to dashboard Cite

We discuss the occurrence of transition structures observed in molecular self-assembly at surfaces. The increasing surface coverage transitions from low coverage structures to high coverage structures are a common phenomenon. However, often observed and not perfectly understood is the formation of intermediate structures, sometimes with lower lateral density than the initial phase. We will present different examples from our recent work and discuss the possible mechanisms of intermediate phase formation. In addition, we present intermediate structures occurring due to temperature-controlled reversible phase transitions.

show abstract

Section: Helical Aromatessupporting

confidence: 76%

Intermediate structures in two-dimensional molecular self-assembly

Ernst

2010

Front. Phys. China

Self Cite

View full text Add to dashboard Cite

show abstract

“…The first 2D sergeant-and-soldiers effect was reported after doping succinic acid monolayers with chiral tartaric acid [159]. Due to the footprint chirality, succinic acid forms enantiomorphous domains on Cu(110), observed as superposition of both enantiomorphs in LEED (Fig.…”

Section: Diastereomers and Diastereomeric Recognitionmentioning

confidence: 97%

Molecular chirality at surfaces

Ernst

2012

Physica Status Solidi (b)

Self Cite

221

264

View full text Add to dashboard Cite

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.

show abstract

“…[72][73][74][75][76] Recent literature cites claims of insignificantly small but still questionable differences seen between chiral isomers in their condensed states, like in supersaturated solutions, in crystals, in micellar aggregates, and on solid surfaces, etc. [77][78][79] Such a finding can have far-reaching implications, since, according to their propositions, these asymmetrical weak nuclear forces propagate to millions of other molecules via weak noncovalent interactions and land-up building asymmetrical population preferring a particular handedness.…”

Section: Homochiral Interaction In Hydrophobic Rod-like Polysilanes: mentioning

confidence: 99%

Nonclassical forces: Seemingly insignificant but a powerful tool to control macromolecular structures

Fujiki

Saxena

2008

J. Polym. Sci. A Polym. Chem.

View full text Add to dashboard Cite

Strong chemical forces such as covalent and ionic bonds are responsible for building discrete molecules, nature dwells on noncovalent forces weaker by three orders in magnitude, like the hydrophobic effect, hydrogen bonding, and van der Waals forces. Despite being weak, they possess the potential to drive spontaneous folding or unfolding of proteins and nucleic acids and the recognition between complimentary molecular surfaces. The power of these forces lies in the cooperativity with which they act, thereby generating a cumulative effect of many bonding interactions occurring together. Many ongoing research aims to translate the potential of these forces to the synthetic world to create desired structures with specific chemical functions. Achieving this offers unlimited opportunities for designing and synthesizing the most complex structures with specific applications. This highlight aims to reflect the critical role these noncovalent forces play in controlling macromolecular structures, which hold immense untapped potential for applications defying conventions, and briefly touches on the concept of homochirality in nature based on chiral and weak noncovalent interactions in synthetic nonpolar Si‐catenated polymers. It sheds some light on the discovery and characterization of Si/F‐C interactions in fluoroalkylated polysilanes in chemosensing of fluoride ions and nitroaromatics with a great sensitivity and selectivity. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 4637–4650, 2008

show abstract

Induction of Homochirality in Achiral Enantiomorphous Monolayers

Cited by 166 publications

References 30 publications

Intermediate structures in two-dimensional molecular self-assembly

Intermediate structures in two-dimensional molecular self-assembly

Molecular chirality at surfaces

Nonclassical forces: Seemingly insignificant but a powerful tool to control macromolecular structures

Contact Info

Product

Resources

About