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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.

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...

The Carbon Cycle

The Carbon Cycle

Carbon is the basis of all organic matter on Earth, and is recycled through the ecosystem in two primary processes: one in which carbon is exchanged among living organisms, and one in which carbon is cycled over long periods of time through fossilized organic remains, weathering of rocks, and volcanic activity. Human activities, including increased agricultural practices and the burning of fossil fuels, has greatly affected the balance of the natural carbon cycle.

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...

Carbon Skeletons

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Life on Earth is carbon-based, as all macromolecules that make up living organisms contain carbon atoms. All organic compounds have a carbon backbone. Each carbon atom is tetravalent and can bond with four other atoms, making it an extraordinarily flexible component of biological molecules. Because carbon’s valence electrons are stable, it rarely becomes an ion. As the carbon chain increases in length, structural modifications such as ring structures, double bonds, and branching side...

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Related Experiment Video

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Chiral Molecular Carbon Nanostructures.

Jesús M Fernández-García¹, Paul J Evans¹, Salvatore Filippone¹

¹Departamento de Química Orgánica, Facultad de Química , Universidad Complutense de Madrid , Avda. Complutense s/n , E-28040 Madrid , Spain.

Accounts of Chemical Research

|June 12, 2019

Summary

Researchers developed methods to synthesize chiral carbon nanostructures, including metallofullerenes, graphene quantum dots, and novel bilayer nanographenes. This advancement enables precise control over chirality in carbon-based materials for diverse applications.

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Area of Science:

Chirality and Nanomaterials Science
Organic and Supramolecular Chemistry

Background:

Chirality is a key molecular property with significant implications in natural and artificial systems.
While chirality is well-established in some molecules, its control in carbon nanostructures like nanotubes and graphene remains a significant challenge.
Existing methods have primarily succeeded in achieving chirality only in empty fullerenes.

Purpose of the Study:

To report progress in the synthesis of various chiral molecular carbon nanostructures.
To introduce novel chiral bilayer nanographenes with enantiomeric control.
To showcase applications of these chiral nanocarbons in catalysis and stereoisomerization studies.

Main Methods:

Asymmetric catalysis for enantioselective synthesis.
Top-down and bottom-up chemical approaches for nanostructure fabrication.
Synthesis of metallofullerenes, endohedral fullerenes, graphene quantum dots (GQDs), and curved molecular nanographenes.
Development of a new family of chiral bilayer nanographenes from helicene precursors.

Main Results:

Successful synthesis of enantiomerically pure metallofullerenes applied as catalysts.
Demonstration of endohedral fullerenes influencing stereoisomerization of pendent groups.
First top-down synthesis of chiral GQDs via functionalization with chiral alcohols.
Synthesis of a single enantiomer of a novel chiral bilayer nanographene, establishing a new class of materials.

Conclusions:

Significant advancements have been made in controlling chirality within diverse carbon nanostructures.
The developed chiral nanocarbons offer new possibilities for structural control and property tuning.
These novel materials hold promise for future applications in catalysis, biomedical science, and materials science.