Structure and Function of Chiral Architectures of Amphiphilic Molecules at the Air/Water Interface

Weissbuch, Isabelle; Leiserowitz, Leslie; Lahav, Meir

doi:10.1002/9783527625345.ch8

Cited by 4 publications

(4 citation statements)

References 64 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Certain amphiphilic prochiral molecules, such as barbituric acid, coumarins, and amphiphilic diacetylenes, self-assemble on aqueous solutions into enantiomorphous crystalline domains, and as reported by Liu et al, these domains were transferred on solid supports to yield homochiral Langmuir−Blodgett films. A special issue on “Molecular Recognition and Chirality in Amphiphilic Assemblies” appeared in “Current Opinion in Colloid & Interface Science” edited by D. Vollhardt and also a chapter in “Chirality at the Nanoscale” a book edited by D. B. Amabilino …”

Section: “Mirror-symmetry Breaking” At Interfacesmentioning

confidence: 99%

Crystalline Architectures as Templates of Relevance to the Origins of Homochirality

2011

Self Cite

View full text Add to dashboard Cite

|Chem. Rev. 2011, 111, 3236-3267 Chemical Reviews REVIEW collaboration in the field of mass spectrometry of peptides and Prof. M. Green for interesting discussions. We thank The Israel Science Foundation for financial support and the European COST 0703 on System Chemistry. This research was made possible in part by the generosity of the Harold Perlmann Family. DEDICATIONDedicated to Prof. H. Kagan on the occasion of his 80th birthday.

show abstract

Section: “Mirror-symmetry Breaking” At Interfacesmentioning

confidence: 99%

Crystalline Architectures as Templates of Relevance to the Origins of Homochirality

2011

Self Cite

View full text Add to dashboard Cite

show abstract

“…However, two examples of chiral expression at the liquid/air interface are briefly mentioned here. 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].…”

Section: Diastereomers and Diastereomeric Recognitionmentioning

confidence: 99%

Molecular chirality at surfaces

Ernst

2012

Physica Status Solidi (b)

223

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

“…Furthermore, other approaches utilize chiral templates or molecular changes affecting the conformation or shape of molecules and nanostructures to spontaneously promote helical structure formation. Examples range from inorganic subnm nanowires and nanocrystals − over polymers − and polymer networks to amphiphiles, surfactants, and a considerable variety of other organic, inorganic, − and organometallic molecules. , …”

mentioning

confidence: 99%

“…Furthermore, other approaches utilize chiral templates 35 or molecular changes affecting the conformation or shape of molecules and nanostructures to spontaneously promote helical structure formation. Examples range from inorganic subnm nanowires 36 and nanocrystals 37−40 over polymers 41−45 and polymer networks 46 to amphiphiles, surfactants, 47 and a considerable variety of other organic, 12 inorganic, 48−50 and organometallic molecules. 51,52 Without delving into the details of molecular parity violations and their role in biomolecular homochirality, 53 the absence of any chiral bias, especially the absence of molecular chirality, 54 results in the formation equal proportions of leftand right-handed molecules or helical (super)structures no matter what the underlying driving force, 55 unless there is an energetic imbalance that gives rise to symmetry breaking.…”

mentioning

confidence: 99%

Molecular Conformation of Bent-Core Molecules Affected by Chiral Side Chains Dictates Polymorphism and Chirality in Organic Nano- and Microfilaments

et al. 2021

View full text Add to dashboard Cite

The coupling between molecular conformation and chirality is a cornerstone in the construction of supramolecular helical structures of small molecules across various length scales. Inspired by biological systems, conformational preselection and control in artificial helical molecules, polymers, and aggregates has guided various applications in optics, photonics, and chiral sorting among others, which are frequently based on an inherent chirality amplification through processes such as templating and self-assembly. The so-called B4 nano- or microfilament phase formed by some bent-shaped molecules is an exemplary case for such chirality amplification across length scales, best illustrated by the formation of distinct nano- or microscopic chiral morphologies controlled by molecular conformation. Introduction of one or more chiral centers in the aliphatic side chains led to the discovery of homochiral helical nanofilament, helical microfilament, and heliconical-layered nanocylinder morphologies. Herein, we demonstrate how a priori calculations of the molecular conformation affected by chiral side chains are used to design bent-shaped molecules that self-assemble into chiral nano- and microfilament as well as nanocylinder conglomerates despite the homochiral nature of the molecules. Furthermore, relocation of the chiral center leads to formation of helical as well as flat nanoribbons. Self-consistent data sets from polarized optical as well as scanning and transmission electron microscopy, thin-film and solution circular dichroism spectropolarimetry, and synchrotron-based X-ray diffraction experiments support the progressive and predictable change in morphology controlled by structural changes in the chiral side chains. The formation of these morphologies is discussed in light of the diminishing effects of molecular chirality as the chain length increases or as the chiral center is moved away from the core-chain juncture. The type of phase (B1-columnar or B4) and morphology of the nano- or microfilaments generated can further be controlled by sample treatment conditions such as by the cooling rate from the isotropic melt or by the presence of an organic solvent in the ensuing colloidal dispersions. We show that these nanoscale morphologies can then organize into a wealth of two- and three-dimensional shapes and structures ranging from flower blossoms to fiber mats formed by intersecting flat nanoribbons.

show abstract

Structure and Function of Chiral Architectures of Amphiphilic Molecules at the Air/Water Interface

Cited by 4 publications

References 64 publications

Crystalline Architectures as Templates of Relevance to the Origins of Homochirality

Crystalline Architectures as Templates of Relevance to the Origins of Homochirality

Molecular chirality at surfaces

Molecular Conformation of Bent-Core Molecules Affected by Chiral Side Chains Dictates Polymorphism and Chirality in Organic Nano- and Microfilaments

Contact Info

Product

Resources

About