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Related Concept Videos

Chirality02:25

Chirality

32.7K
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...
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Chirality in Nature02:30

Chirality in Nature

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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.
18.2K
Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

16.6K
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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Prochirality02:05

Prochirality

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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 at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

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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...
7.5K
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

12.0K
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,...
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Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
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Synergistic Chirality in Spiro-Fused Chiral Conjugated Helices.

Jiangtao Chan1,2, Zelong Liu3, Zixin Liu2

  • 1School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing, 100049, China.

Angewandte Chemie (International Ed. in English)
|April 11, 2026
PubMed
Summary

Researchers designed novel spiro-fused chiral conjugated helices, revealing how mixed chiral centers influence chirality. This breakthrough offers new strategies for developing advanced chiroptical materials.

Keywords:
chiral conjugated helicesmulti‐chiral‐centersrotatory strengthspiro‐fused polycyclic aromatic hydrocarbonssynergistic chirality

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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Chirality is crucial in molecular recognition and materials science.
  • Designing molecules with predictable chiroptical properties remains a challenge.
  • Spirodiperylenetetraimide (SDP) scaffolds offer a promising platform for complex chiral structures.

Purpose of the Study:

  • To synthesize novel spiro-fused chiral conjugated helices using a bilateral bent-π-extension strategy.
  • To investigate chirality synergy across multiple chiral centers within these novel structures.
  • To understand the relationship between molecular structure and chiroptical response.

Main Methods:

  • Bilateral bent-π-extension strategy for synthesis.
  • Resolution of six stereoisomers of spirodiperylenetetraimide-based helicenes (SDPD6H).
  • Single-crystal X-ray diffraction for structural analysis.
  • Chiroptical spectroscopy (Circular Dichroism) and theoretical calculations (rotatory strength).

Main Results:

  • Successful synthesis and resolution of six stereoisomers of SDPD6H.
  • Helicene fusion induced bending of planar perylene diimide subunits, increasing isomerization barriers.
  • Distinct chiroptical responses observed, with P,S,P-6 exhibiting the strongest activity (|Δε| up to 310 M⁻¹ cm⁻¹).
  • Theoretical analysis revealed that homochiral configurations yield pronounced CD signals due to non-canceling magnetic transition dipole moments, while heterochiral configurations show suppressed CD signals.

Conclusions:

  • The study establishes a new design strategy for spiro-fused chiral conjugated helices.
  • Mechanistic understanding of stereochemical interplay in multi-chiral-center systems was achieved.
  • These findings pave the way for developing advanced chiroptical materials with tunable properties.