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Chirality

Chirality

Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...

Molecules with Multiple Chiral Centers

Molecules with Multiple Chiral Centers

Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...

Chirality in Nature

Chirality in Nature

Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.

Prochirality

Prochirality

The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...

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Related Experiment Video

Updated: May 7, 2025

Self-assembly of Complex Two-dimensional Shapes from Single-stranded DNA Tiles

Self-assembly of Complex Two-dimensional Shapes from Single-stranded DNA Tiles

Published on: May 8, 2015

An aperiodic chiral tiling by topological molecular self-assembly.

Jan Voigt¹, Miloš Baljozović¹, Kévin Martin²

¹Empa, Swiss Federal Laboratories for Materials Science and Technology, Dübendorf, Switzerland.

Nature Communications

|January 3, 2025

Summary

Chiral molecules self-assemble into aperiodic triangular tilings on silver surfaces. Topological constraints and intermolecular forces drive this unique two-dimensional molecular aggregation, forming distinct defects and supramolecular spirals.

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Area of Science:

Surface science
Crystallization fundamentals
Supramolecular chemistry

Background:

Two-dimensional self-assembly of chiral molecules is key to understanding crystallization.
Polyaromatic chiral molecules exhibit unique aggregation behaviors on surfaces.

Purpose of the Study:

To investigate the uncommon aggregation of polyaromatic chiral molecules on a silver surface.
To understand the role of topological constraints and intermolecular forces in driving aperiodic tiling.

Main Methods:

Scanning tunneling microscopy (STM) was employed to examine molecular aggregation.
Analysis of molecular packing, tiling patterns, and defect formation.

Main Results:

Chiral molecules formed dense, chiral triangular tilings of triads on a silver surface.
A random distribution of mirror-isomers was observed within triangles, with an excess of one isomer.
Topological defects at domain boundaries, driven by chirality, led to supramolecular spirals.
Observed tiling was aperiodic, differing from known patterns like Penrose tiling.

Conclusions:

Two-dimensional molecular self-assembly can be dictated by topological constraints.
Intermolecular forces play a crucial role in inducing aperiodic tiling.
Entropy maximization influences the arrangement of chiral molecules.