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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 in Nature

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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

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...

Photochemical Electrocyclic Reactions: Stereochemistry

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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
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Molecules with Multiple Chiral Centers

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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...

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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...

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Related Experiment Video

Updated: Feb 28, 2026

Resonance Fluorescence of an InGaAs Quantum Dot in a Planar Cavity Using Orthogonal Excitation and Detection

Resonance Fluorescence of an InGaAs Quantum Dot in a Planar Cavity Using Orthogonal Excitation and Detection

Published on: October 13, 2017

Chirality Control of Electron Transfer in Quantum Dot Assemblies.

Brian P Bloom¹, Brittney M Graff¹, Supriya Ghosh¹

¹Department of Chemistry, University of Pittsburgh , Pittsburgh, Pennsylvania 15260, United States.

Journal of the American Chemical Society

|June 14, 2017

Summary

Molecular chirality significantly impacts electron transfer rates between quantum dots (QDs). The study reveals that both light polarization and QD chirality influence electron transfer kinetics, offering new control over charge flow.

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Area of Science:

Molecular electronics
Quantum dot assemblies
Chirality-directed charge transport

Background:

Electron spin and molecular chirality are key factors for controlling charge flow at the nanoscale.
Quantum dots (QDs) offer a versatile platform for studying charge transfer phenomena.

Purpose of the Study:

To investigate the influence of molecular chirality on electron transfer rates between quantum dots.
To explore the role of light polarization and QD chirality in electron transfer kinetics.

Main Methods:

Fabrication of chiral quantum dot assemblies.
Excitation of electron donors with circularly polarized light.
Measurement of electron transfer rates between quantum dots.
Analysis of circular dichroism (CD) spectra of QDs.

Main Results:

Molecular chirality induces order-of-magnitude effects on electron transfer rates in QD assemblies.
Both excitation light polarization and acceptor QD chirality modulate electron transfer kinetics.
A polarization for the electron transfer rate constant was defined and correlated with acceptor QD CD spectrum strength.

Conclusions:

The circular dichroism (CD) strength of QD exciton transitions can predict spin-dependent electron transfer.
Chiral imprinting of quantum dots is likely the underlying mechanism for spin-dependent electron transfer.
These findings open avenues for designing chiral molecular systems for controlled charge transport.