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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...

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.

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...

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...

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...

Radicals: Electronic Structure and Geometry

Radicals: Electronic Structure and Geometry

This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...

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Related Experiment Video

Updated: Jan 4, 2026

Microscopic Visualization of Porous Nanographenes Synthesized through a Combination of Solution and On-Surface Chemistry

Microscopic Visualization of Porous Nanographenes Synthesized through a Combination of Solution and On-Surface Chemistry

Published on: March 4, 2021

Chirality-Embedded Nanographenes.

Shohei Nishitani¹, Ryo Sekiya¹, Takeharu Haino¹

¹Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, 739-8526, Japan.

Angewandte Chemie (International Ed. in English)

|November 1, 2019

Summary

Chiral functional groups attached to nanographene edges create surface chirality. This chirality transfer, confirmed by X-ray diffraction and DFT, reveals insights into top-down nanographene edge structures.

Keywords:

chirality exciton coupling graphene graphene quantum dots nanographenes

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Published on: March 4, 2021

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Assembly of Gold Nanorods into Chiral Plasmonic Metamolecules Using DNA Origami Templates

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Published on: March 5, 2019

Area of Science:

Organic Chemistry
Materials Science
Nanotechnology

Background:

Chiral nanographenes are typically synthesized using bottom-up approaches.
Developing chiral nanographenes via post-modification of top-down synthesized nanographenes is less common.

Purpose of the Study:

To demonstrate the generation of surface chirality on nanographenes through the attachment of chiral functional groups.
To investigate the mechanism of chirality transfer from functional groups to the nanographene surface.
To elucidate the edge structure of top-down synthesized nanographenes.

Main Methods:

Post-modification of nanographenes with chiral functional groups.
X-ray diffraction analysis.
Density Functional Theory (DFT) calculations.
Analysis of exciton coupling between functional groups.

Main Results:

Attachment of chiral functional groups to nanographene edges successfully induces surface chirality.
Chirality transfer occurs via steric interactions from the chiral center through a cyclic imide to the nanographene edge.
Exciton coupling indicates specific arrangement and orientation of functional groups on armchair edges.

Conclusions:

Top-down synthesized nanographenes can be rendered chiral by edge functionalization.
The study provides a method to understand the surface structure and chirality of nanographenes.
This work contributes to the development of chiral nanographene materials.