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Related Concept Videos

Chirality02:25

Chirality

32.2K
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...
32.2K
Prochirality02:05

Prochirality

5.4K
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...
5.4K
Chirality in Nature02:30

Chirality in Nature

17.9K
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.
17.9K
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

7.4K
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...
7.4K
Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

16.4K
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...
16.4K
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

11.9K
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,...
11.9K

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Related Experiment Video

Updated: Mar 28, 2026

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

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A supramolecular helix that disregards chirality.

Cécile Roche1, Hao-Jan Sun1,2, Pawaret Leowanawat1

  • 1Roy &Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.

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Complex crystalline systems can form ordered structures from racemic mixtures, challenging previous assumptions. A novel cogwheel mechanism enables self-assembly into helical supramolecular structures regardless of chirality.

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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Controlling the Size, Shape and Stability of Supramolecular Polymers in Water
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Area of Science:

  • Supramolecular chemistry
  • Materials science
  • Crystallography

Background:

  • Complex crystalline systems typically require homochiral building blocks for ordered structures.
  • Heterochiral and racemic compounds often result in disordered materials.
  • Chirality is generally considered crucial for achieving high crystalline order.

Purpose of the Study:

  • To investigate the self-assembly behavior of perylene bisimide derivatives with varying enantiomeric purity.
  • To explore the formation of ordered crystalline structures from racemic and homochiral perylene bisimides.
  • To elucidate the mechanism behind the observed crystalline order in helical assemblies.

Main Methods:

  • Synthesis of perylene bisimide derivatives.
  • Supramolecular self-assembly experiments.
  • Single-crystal X-ray diffraction analysis.
  • Chiral analysis of the resulting assemblies.

Main Results:

  • Perylene bisimide derivatives self-assembled into helical structures regardless of enantiomeric purity.
  • Both homochiral and racemic compounds formed columnar hexagonal crystalline domains with single-crystal-like order.
  • A mixture of 21 diastereomers also yielded highly ordered helical assemblies.
  • A cogwheel mechanism was proposed to explain the chirality-independent ordering.

Conclusions:

  • Chirality is not always a prerequisite for forming highly ordered crystalline systems.
  • A novel cogwheel mechanism facilitates the self-assembly of racemic and homochiral building blocks into ordered helical structures.
  • This finding opens new avenues for creating complex crystalline materials from readily available racemic precursors.