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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...

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.

Polymer Classification: Stereospecificity

Polymer Classification: Stereospecificity

Polymerization generates chiral centers along the entire backbone of a polymer chain. Accordingly, the stereochemistry of the substituent group has a significant effect on polymer properties. Polymers formed from monosubstituted alkene monomers feature chiral carbons at every alternate position in the polymer backbone. Relative to the predominant orientation of substituents at the adjacent chiral carbons, the polymer can exist in three different configurations: isotactic, syndiotactic, and...

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...

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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

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Chiral supramolecular polymers.

Fátima García¹, Rafael Gómez¹, Luis Sánchez¹

¹Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Ciudad Universitaria s/n, 28040-Madrid, Spain. lusamar@ucm.es.

Chemical Society Reviews

|October 11, 2023

Summary

Chiral supramolecular polymers (SPs) are synthesized using chiral monomers or external stimuli. These helical structures offer insights into natural homochirality and new organic material functionalities.

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Published on: February 15, 2016

Area of Science:

Supramolecular Chemistry
Polymer Science
Organic Materials

Background:

Chiral supramolecular polymers (SPs) are crucial for understanding natural homochirality and developing advanced organic materials.
Helical structures in SPs serve as models for fundamental chirality studies.

Purpose of the Study:

To review strategies for constructing chiral supramolecular polymers.
To highlight methods for transferring chirality from monomers to polymers and inducing chirality in achiral systems.
To present applications of chiral SPs.

Main Methods:

Utilizing chiral monomeric units to build chiral SPs.
Employing external stimuli (stirring, solvent, light) to induce chirality in achiral systems.
Analyzing thermodynamic and kinetic factors influencing asymmetry amplification.

Main Results:

Demonstration of efficient chirality transfer from monomers to supramolecular scaffolds, yielding enantioenriched helical structures.
Examples of symmetry breaking in achiral systems to form chiral SPs via external stimuli.
Overview of thermodynamic and kinetic influences on asymmetry amplification in co-assembly.

Conclusions:

Chiral SPs can be effectively constructed through monomer-based or stimulus-induced approaches.
Understanding thermodynamics and kinetics is key for controlling asymmetry amplification.
Chiral SPs hold significant promise for diverse applications in organic materials.