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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...

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...

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

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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: Mar 27, 2026

Nanofabrication of Gate-defined GaAs/AlGaAs Lateral Quantum Dots

Nanofabrication of Gate-defined GaAs/AlGaAs Lateral Quantum Dots

Published on: November 1, 2013

Chiral Graphene Quantum Dots.

Nozomu Suzuki¹, Yichun Wang, Paolo Elvati

¹Graduate School of Materials Science, Nara Institute of Science and Technology , Ikoma, Nara 8916-5, Japan.

|January 9, 2016

Summary

This summary is machine-generated.

Covalent attachment of cysteine to graphene quantum dots (GQDs) induces helical buckling, creating nanoscale chirality. These chiral GQDs exhibit distinct circular dichroism signals and differential cellular interactions, impacting their biocompatibility and toxicity.

Keywords:

biological activity chiral excitons chirality circular dichroism graphene quantum dots

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Area of Science:

Nanotechnology
Materials Science
Biochemistry

Background:

Chiral nanostructures are crucial for polarization-enabled optoelectronics.
Graphene-based materials offer unique properties for chiral nanostructures.
Covalent modification of graphene quantum dots (GQDs) can introduce novel functionalities.

Purpose of the Study:

To investigate the creation of nanoscale chirality in graphene quantum dots (GQDs).
To characterize the chiroptical properties of cysteine-functionalized GQDs.
To evaluate the biocompatibility and cellular interactions of chiral GQDs.

Main Methods:

Covalent attachment of l/d-cysteine to GQD edges.
Circular dichroism (CD) spectroscopy to analyze chiroptical properties.
Density functional theory (DFT) and molecular dynamics (MD) simulations.
In vitro cell exposure studies with liver HepG2 cells.

Main Results:

Cysteine attachment induced helical buckling and nanoscale chirality in GQDs.
CD spectra revealed distinct bands corresponding to chiral interactions and 3D twisting.
L/D-GQDs showed general biocompatibility but differed in cellular membrane accumulation and toxicity.
d-GQDs exhibited stronger cellular membrane accumulation than L-GQDs.

Conclusions:

Covalent functionalization is an effective strategy to induce nanoscale chirality in GQDs.
Chiral GQDs possess unique chiroptical signatures and stereoisomer-specific cellular interactions.
The emergence of nanoscale chirality in flexible nanomaterials decorated with biomolecules is a general phenomenon.