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Related Concept Videos

Prochirality02:05

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...
Fischer Projections02:18

Fischer Projections

Learning to draw Fischer projections of molecules and understanding their relevance plays a crucial role in the visual depiction of organic molecules. A Fischer projection is a two-dimensional projection on a planar surface to simplify the three-dimensional wedge–dash representation of molecules. This is especially helpful in the case of molecules with multiple chiral centers that can be difficult to draw. Here, all the bonds of interest are represented as horizontal or vertical lines. While...
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this staggered...
Stereoisomerism02:52

Stereoisomerism

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...
Molecules with Multiple Chiral Centers02:25

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...
Chirality02:25

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...

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Related Experiment Video

Updated: Jul 5, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

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

Published on: February 15, 2016

Coordination-driven face-directed self-assembly of trigonal prisms. Face-based conformational chirality.

Douglas C Caskey1, Takuya Yamamoto, Chris Addicott

  • 1Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, USA.

Journal of the American Chemical Society
|May 22, 2008
PubMed
Summary

Researchers created chiral trigonal prisms using platinum linkers and star connectors. Chirality transfer was observed, with distinct pyridine ring edge behaviors and temperature-dependent interconversion dynamics.

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Last Updated: Jul 5, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

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Published on: February 15, 2016

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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

Published on: February 7, 2017

Area of Science:

  • Supramolecular Chemistry
  • Coordination Chemistry
  • Materials Science

Background:

  • Coordination-driven self-assembly is a powerful method for constructing complex molecular architectures.
  • Trigonal prisms represent a fundamental polyhedral structure with potential applications in molecular recognition and catalysis.

Purpose of the Study:

  • To synthesize and characterize novel trigonal prisms using a face-directed self-assembly approach.
  • To investigate the influence of conformationally chiral star connectors on the resulting prism's chirality.
  • To study the dynamic behavior of the pyridine ring edges within the assembled prisms.

Main Methods:

  • Synthesis of four different trigonal prisms via coordination-driven self-assembly.
  • Characterization using multinuclear and DOSY NMR, and dual ESI-FT-ICR mass spectrometry.
  • Computational analysis using molecular mechanics.
  • Kinetic studies via line-shape analysis and 1-D EXCHSY NMR for edge interconversion.

Main Results:

  • High yields of four distinct trigonal prisms were achieved without template assistance.
  • Chirality was successfully communicated from the star connector to the prism, demonstrating chirality transfer.
  • NMR data confirmed distinct pyridine ring edges and revealed temperature-dependent interconversion dynamics.
  • Two distinct activation energies for pyridine ring rotation were observed, suggesting complex dynamic behavior.

Conclusions:

  • The face-directed self-assembly is an efficient route to complex chiral supramolecular structures.
  • Conformationally chiral building blocks can induce chirality in polyhedral assemblies.
  • The dynamic behavior of the prism edges is complex and exhibits temperature-dependent transitions.