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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...

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...

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...

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: Sep 17, 2025

A Micropatterning Assay for Measuring Cell Chirality

A Micropatterning Assay for Measuring Cell Chirality

Published on: March 11, 2022

Chirality Unbound in Graphene Nanoribbons.

Si Tong Bao¹, Yongseok Hong¹, Haoyu Jiang¹

¹Department of Chemistry, Columbia University, New York, New York, 10027, USA.

Angewandte Chemie (International Ed. in English)

|June 27, 2025

Summary

Researchers synthesized ultralong, chiral graphene nanoribbons (GNRs) with controlled helical twisting. These GNRs show record-breaking circular dichroism and function as room-temperature spin filters, paving the way for new chiroptical materials.

Keywords:

Chirality Chiral‐induced spin selectivity Graphene nanoribbons Ladder polymers

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Area of Science:

Materials Science
Organic Chemistry
Nanotechnology

Background:

Graphene nanoribbons (GNRs) are promising materials with tunable electronic properties.
Achieving controlled chirality and extended helical structures in GNRs remains a significant challenge.

Purpose of the Study:

To demonstrate controlled helicity in extended graphene nanoribbons.
To develop a high-yielding synthetic method for chiral GNRs.
To investigate the chiroptical properties and spin-filtering capabilities of these novel GNRs.

Main Methods:

Synthesis of defect-free, ultralong, chiral cove-edged GNRs using a robust method.
Tuning helical twisting of the GNR backbone via functionalization with chiral side chains.
Characterization of structural, chiroptical, and spin-selective properties.

Main Results:

Demonstrated controlled, tunable helical twisting in extended GNRs.
Synthesized GNRs up to 65 nm in length with nearly 10 helical rotations.
Achieved an unprecedented circular dichroic response (|Δε| = 6780 M⁻¹ cm⁻¹ at 550 nm).
Observed room-temperature spin filtering in thin films due to chirality-induced spin selectivity.

Conclusions:

Established a new synthetic route for creating extended chiral GNRs with controlled helicity.
Developed a novel chiroptical material with the highest recorded circular dichroic response for organic molecules.
Showcased the potential of these GNRs as efficient room-temperature spin filters.