Stereochemical studies on chiral systems in two dimensions

Weissbuch, Isabelle; Kuzmenko, Ivan; Berfeld, Maria; Leiserowitz, Leslie; Lahav, Meir

doi:10.1002/1099-1395(200007)13:7<426::aid-poc265>3.0.co;2-#

Cited by 36 publications

(24 citation statements)

References 33 publications

(21 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…More examples can be found in topical reviews [231,232]. Using chiral amphiphilic molecules 2D crystallization has been studied with grazing incidence synchrotron X-ray diffraction (GIXD) [233]. It has been shown that long-alkyl chain a amino acids self-organize into 2-D crystals in which the two enantiomers either form heterochiral domains or spontaneously separate into enantiomorphous islands composed of homochiral molecules.…”

Section: Diastereomers and Diastereomeric Recognitionmentioning

confidence: 95%

“…Moreover, diastereomeric acid-base interactions between different chiral amphiphiles induced spontaneous chiral separation at the liquid/air interface. The enantioselective interaction of chiral solutes with the molecules assembled at the surface via Cu-complexation revealed that R-S complexes could be packed more densely than S-S or R-R diastereomers [233].…”

Section: Diastereomers and Diastereomeric Recognitionmentioning

confidence: 99%

See 1 more Smart Citation

Molecular chirality at surfaces

Ernst

2012

Physica Status Solidi (b)

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

Section: Diastereomers and Diastereomeric Recognitionmentioning

confidence: 95%

Section: Diastereomers and Diastereomeric Recognitionmentioning

confidence: 99%

Molecular chirality at surfaces

Ernst

2012

Physica Status Solidi (b)

221

264

View full text Add to dashboard Cite

show abstract

“…24,25 The density of chiral centers in those monolayers is, however, much higher than the density of the chiral centers protruding to the liquid from the monolayer of (S)-1. We cannot exclude that in our case adjacent 2-methylbutoxy groups still interact.…”

mentioning

confidence: 99%

Losing the Expression of Molecular Chirality in Self-Assembled Physisorbed Monolayers

et al. 2005

View full text Add to dashboard Cite

show abstract

“…Chiral molecular monolayers are appealing from a number of viewpoints 1–3. The formation of enantiopure layers leads to unique structures that are of interest with respect to the evolution of (among other things) chiral structures in bulk systems,4 their optical properties,5 and their interactions with biological systems 6.…”

Section: Introductionmentioning

confidence: 99%

“…Chiral molecular monolayers are appealing from a number of viewpoints. [1][2][3] The formation of enantiopure layers leads to unique structures that are of interest with respect to the evolution of (among other things) chiral structures in bulk systems, [4] their optical properties, [5] and their interactions with biological systems. [6] Our focus concerns the crystallization of materials onto self-assembled monolayers (SAMs), a topic that is receiving increasing attention because it is a way to restrict the crystallization process so that small monoA C H T U N G T R E N N U N G crystals of different shapes can be prepared, [7] and even influence the polymorph that is formed.…”

Section: Introductionmentioning

confidence: 99%

A Chiral Self‐Assembled Monolayer Derived from a Resolving Agent and its Performance as a Crystallization Template for an Organic Compound from Organic Solvents

Bejarano‐Villafuerte

Meijden

Lingenfelder

et al. 2012

Chemistry A European J

View full text Add to dashboard Cite

A new chiral nonracemic thiol derived from a popular acidic resolving agent that incorporates a cyclic disubstituted phosphate group (phencyphos) has been prepared in enantiomerically pure form. The stereochemistry and absolute configuration were established by performing a single-crystal X-ray structural analysis of a synthetic intermediate. The thiol compound was used for the preparation of self-assembled monolayers (SAMs) on both monocrystalline and polycrystalline metallic gold, which have very different surface roughness. The monolayers were used to promote the nucleation and growth of crystals from nonaqueous solutions of an organic molecule (the parent phencyphos) of similar structure to the compound present in the monolayer. The template layers influence the nucleation and growth of the phencyphos crystals despite the lack of two-dimensional order in the surfaces. Heterogeneous nucleation of phencyphos takes place upon evaporation of either CHCl(3) or isopropanol solutions of the compound on the SAM surfaces, where the evaporation rate merely influences the size and homogeneity of the crystals. The roughness of the surface also plays an important role; the polycrystalline gold produces more homogeneous samples because of the greater number of nucleation sites. Clear evidence for nucleation and growth on the surfaces is shown by scanning electron microscopy. The variation in crystal form achieved by using different surfaces and solvents suggests that the layers are applicable for the preparation of organic crystals from organic solutions.

show abstract

Stereochemical studies on chiral systems in two dimensions

Cited by 36 publications

References 33 publications

Molecular chirality at surfaces

Molecular chirality at surfaces

Losing the Expression of Molecular Chirality in Self-Assembled Physisorbed Monolayers

A Chiral Self‐Assembled Monolayer Derived from a Resolving Agent and its Performance as a Crystallization Template for an Organic Compound from Organic Solvents

Contact Info

Product

Resources

About