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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...

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...

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...

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. The...

Crystallographic Point Groups

Crystallographic Point Groups

Crystallographic point groups represent the various symmetry operations that can occur within crystals. They are unique in that at least one point will always remain unchanged during these actions. For instance, consider the triclinic system. This system, devoid of any axis or plane of symmetry, aligns with the C1 and Ci point groups.where Cᵢ is characterized solely by a center of inversion.Contrastingly, the monoclinic system introduces an element of symmetry. This system with one plane and...

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Related Experiment Video

Updated: May 23, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Chiral pinwheel clusters lacking local point chirality.

Kai Sun¹, Ting-Na Shao, Jia-Le Xie

¹School of Physical Science and Technology & MOE Key Laboratory on Luminescence and Realtime Analysis, Southwest University, Chongqing, P.R. China.

Small (Weinheim an Der Bergstrasse, Germany)

|April 19, 2012

Summary

Pentacene molecules self-assemble into chiral pinwheel clusters on a bismuth surface, demonstrating two levels of chirality. Local point chirality is not essential for forming these large, organized 2D supramolecular structures.

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Last Updated: May 23, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

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Published on: February 15, 2016

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Published on: February 7, 2017

Area of Science:

Supramolecular Chemistry
Surface Science
Materials Science

Background:

Supramolecular pinwheel clusters are chiral structures formed by molecules with polar groups.
These structures rely on strong intermolecular interactions like hydrogen bonding or dipole interactions.

Purpose of the Study:

To investigate the self-assembly of pentacene into chiral pinwheel clusters on the Bi(111) surface.
To explore the role of intermolecular interactions in the formation of these structures.
To identify new relationships between local point chirality and organizational chirality.

Main Methods:

Utilizing scanning tunneling microscopy (STM) for surface analysis.
Investigating the self-assembly behavior of pentacene on the Bi(111) surface.
Analyzing molecular arrangements and chiral properties.

Main Results:

Pentacene, a linear aromatic molecule, self-assembles into large chiral pinwheel clusters on the Bi(111) surface.
Two distinct levels of organizational chirality were observed: chiral hexamers and a chiral arrangement of these hexamers.
Demonstrated that local point chirality is not a prerequisite for the formation of organizational chirality in these 2D clusters.

Conclusions:

Pentacene's self-assembly on Bi(111) leads to complex chiral supramolecular structures.
The study reveals a novel relationship where organizational chirality can emerge independently of local point chirality.
Highlights the potential for designing chiral materials from achiral building blocks through surface-mediated self-assembly.