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Related Concept Videos

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...
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SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

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In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
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SN1 Reaction: Stereochemistry02:15

SN1 Reaction: Stereochemistry

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This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
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Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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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.
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Pathway-directed recyclable chirality inversion of coordinated supramolecular polymers.

Kuo Fu1, Yanli Zhao2, Guofeng Liu3,4

  • 1School of Chemical Science and Engineering, Advanced Research Institute, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University, Shanghai, 200092, P. R. China.

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Researchers developed metal-ion systems to control dynamic chirality inversion in supramolecular materials. This breakthrough enables pathway-directed assembly and offers new possibilities for chiral spintronics and data encryption.

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Chirality Studies

Background:

  • Dynamic chirality inversion in complex supramolecular assemblies remains poorly understood.
  • Controlling pathway complexity is crucial for designing advanced functional materials.

Purpose of the Study:

  • To establish metal-ion driven assembly systems for pathway-directed chirality inversion.
  • To investigate assembly polymorphism and recyclability in supramolecular materials.
  • To explore applications in data encryption and chiral spintronics.

Main Methods:

  • Metal coordination-driven self-assembly using pyridyl-conjugated cholesterol (PVPCC) and metal ions (Ag+, Al3+).
  • Analysis of competitive and solvent-assisted consecutive pathways.
  • Characterization of chiroptical properties and assembly states (Ag-SP I, Ag-SP II, Al-SP I, Al-SP II).
  • Demonstration of solid-state chirality inversion and circularly polarized luminescence encryption.

Main Results:

  • Ag(I)/PVPCC system exhibits a competitive pathway leading to kinetically controlled (Ag-SP I) or thermodynamically favored (Ag-SP II) structures with reversible chiroptical inversion.
  • Al(III)/PVPCC system shows a solvent-assisted pathway, converting an ethanol-containing intermediate (Al-SP II) to an ethanol-free form (Al-SP I) with opposite chiroptical properties upon heating.
  • Stable solid-state chirality inversion was achieved, enabling dynamic circularly polarized luminescence encryption when co-assembled with thioflavin T.

Conclusions:

  • Metal coordination provides a powerful strategy for controlling dynamic chirality inversion and polymorphism in supramolecular assemblies.
  • The demonstrated pathway-directed and recyclable chirality modulation offers significant potential for advanced applications.
  • Findings guide the development of supramolecular materials for information processing, data encryption, and chiral spintronics.