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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.

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...

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...

Stereoisomerism of Cyclic Compounds

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...

Stereoisomerism

Stereoisomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...

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...

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Updated: May 27, 2025

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

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Published on: February 7, 2017

Engineering Helical Chirality in Metal-Coordinated Cyclodextrin Nanochannels.

Zhiyuan Jiang¹, Zhi Chen², Xiujun Yu²

¹Department of Chemistry, The University of Hong Kong, Hong Kong, Hong Kong SAR 999077, China.

Journal of the American Chemical Society

|February 18, 2025

Summary

Researchers created novel silver-ion (Ag+) helicates using cyclodextrin-based ligands. These artificial nanochannels exhibit controllable geometry and helicity, paving the way for advanced nanostructures.

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Published on: September 18, 2016

Area of Science:

Supramolecular Chemistry
Nanotechnology
Coordination Chemistry

Background:

Helicates are crucial in biological systems (DNA, proteins).
Cyclodextrins are promising for building helical structures.
Lack of controllable tools hinders artificial helical nanochannel construction.

Purpose of the Study:

To develop artificial helical nanochannels with controllable geometry and helicity.
To utilize cyclodextrin-derived ligands and silver ions for nanochannel assembly.
To explore the influence of metal coordination geometry on helicity.

Main Methods:

Assembly of Ag6L2 helical nanochannels from alpha-cyclodextrin-derived ligands.
Coordination chemistry involving pyridinyl groups and Ag+ cations.
Modulation of nanochannel helicity by altering ligand substituents (methyl groups).
Theoretical calculations to support experimental findings.

Main Results:

Successfully synthesized Ag6L2 helical nanochannels with controllable M or P helicity.
Tetrahedral Ag+ coordination promotes helicity; linear coordination diminishes it.
Ligand modification precisely controls nanochannel geometry and helicity.
Formation of a 2D coordinative network with hexagonal tessellation.

Conclusions:

Demonstrated facile assembly of tunable helical nanochannels using cyclodextrin-based ligands and silver ions.
Precise control over nanochannel helicity and geometry is achievable.
The findings offer a new platform for designing advanced helical nanostructures.