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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...

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...

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...

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.

Radical Halogenation: Stereochemistry

Radical Halogenation: Stereochemistry

Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:

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Engineering Molecular Recognition with Bio-mimetic Polymers on Single Walled Carbon Nanotubes

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Postclustering dynamic covalent modification for chirality control and chiral sensing.

Yang Yang¹, Xiao-Li Pei, Quan-Ming Wang

¹State Key Lab of Physical Chemistry of Solid Surfaces Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University , Xiamen, Fujian, People' s Republic of China.

Journal of the American Chemical Society

|October 2, 2013

Summary

This summary is machine-generated.

Researchers developed a new method to create functional materials using gold-silver clusters. This postclustering modification (PCM) strategy enables chiral recognition and property tuning in advanced materials.

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Area of Science:

Inorganic Chemistry
Materials Science
Supramolecular Chemistry

Background:

Cluster-based functional materials offer tunable structures and properties.
Postclustering modification (PCM) allows property tailoring via cluster functional group modification.

Purpose of the Study:

To synthesize a novel gold-silver cluster with reactive sites for postclustering modification.
To achieve chirality transfer from chiral monoamines to the gold-silver cluster.
To explore the application of these chiral clusters in chiral recognition and enantiomeric excess (ee) determination.

Main Methods:

Synthesis of a gold-silver cluster functionalized with aldehydes using a protection-deprotection strategy.
Postclustering modification (PCM) via dynamic covalent imine bond formation with chiral monoamines.
Confirmation of homochirality using X-ray structural determination and Circular Dichroism (CD) spectroscopy.

Main Results:

A new gold-silver cluster with six reactive aldehyde sites was successfully synthesized.
Chirality was effectively transferred from chiral monoamines to the gold-silver cluster, forming homochiral clusters.
Intense CD signals were observed, demonstrating the potential for chiral recognition and ee value determination.

Conclusions:

The prefunctionalization of clusters and the PCM strategy provide a versatile approach for designing functional cluster materials.
This method opens new avenues for creating advanced materials with tailored properties and applications in chiral sensing.