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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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Radicals: Electronic Structure and Geometry01:07

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This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
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Chirality at Nitrogen, Phosphorus, and Sulfur02:30

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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...
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Molecules with Multiple Chiral Centers02:25

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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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Stereoisomerism02:52

Stereoisomerism

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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...
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Naming Enantiomers02:21

Naming Enantiomers

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The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system essentially comprises three...
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Related Experiment Video

Updated: Mar 22, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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Chiral Redox-Active Isosceles Triangles.

Siva Krishna Mohan Nalluri1, Zhichang Liu1, Yilei Wu1

  • 1Department of Chemistry and ‡Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University , 2145 Sheridan Road, Evanston, Illinois 60208-3113, United States.

Journal of the American Chemical Society
|April 13, 2016
PubMed
Summary
This summary is machine-generated.

Researchers developed rigid chiral triangles from pyromellitic diimide (PMDI) and naphthalene diimide (NDI) units for energy storage. These materials exhibit unique stacking and electron sharing, improving organic rechargeable lithium-ion battery performance with increased NDI content.

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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Electrochemistry
  • Energy Storage

Background:

  • Small-molecule organic redox-active materials are crucial for advanced energy storage applications.
  • Designing novel molecular architectures with tailored electronic properties is an ongoing challenge.
  • Previous research focused on equilateral triangles with identical redox units.

Purpose of the Study:

  • To synthesize and characterize novel rigid chiral isosceles triangles composed of non-identical pyromellitic diimide (PMDI) and naphthalene diimide (NDI) redox units.
  • To investigate the solid-state structures, electronic properties, and supramolecular assembly of these new materials.
  • To evaluate their performance as electrode-active materials in organic rechargeable lithium-ion batteries.

Main Methods:

  • Synthesis and characterization using NMR and single-crystal X-ray diffraction.
  • Electrochemical analysis via cyclic voltammetry.
  • Electron paramagnetic resonance (EPR) and electron-nuclear double-resonance (ENDOR) spectroscopy, supported by DFT calculations.

Main Results:

  • Two rigid chiral isosceles triangles with C2 symmetry and triangular prism-like geometries were successfully synthesized.
  • Unlike equilateral triangles, these isosceles triangles formed specific NDI-NDI and NDI-PMDI π-π stacked dimers with opposite helicities.
  • The materials exhibited reversible multi-electron acceptance (up to six electrons), with unpaired electrons selectively shared among NDI subunits.
  • Increased NDI content in the molecular structure correlated with improved electrochemical cell performance in lithium-ion batteries.

Conclusions:

  • Rigid chiral isosceles triangles based on PMDI and NDI are promising redox-active materials for organic batteries.
  • Molecular design, specifically the ratio of NDI to PMDI units, significantly influences solid-state packing and electrochemical performance.
  • These findings provide valuable structure-property relationships for developing next-generation organic energy storage materials.