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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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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.
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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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Isomerism in Complexes
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Updated: May 16, 2025

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Homochiral versus Racemic 2D Covalent Organic Frameworks.

José Del Refugio Monroy1,2, Tejas Deshpande3, Joël Schlecht2

  • 1Department of Chemistry & Center for the Science of Materials Berlin, Humboldt-Universität zu Berlin, Brook-Taylor-Strasse 2, Berlin 12489, Germany.

Journal of the American Chemical Society
|May 15, 2025
PubMed
Summary
This summary is machine-generated.

Researchers created chiral two-dimensional covalent organic frameworks ([5]HeliCOFs) using [5]helicene building blocks. These novel frameworks exhibit unique chiroptical and photoluminescent properties, advancing chiral material science.

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Synthesizing homochiral 2D covalent organic frameworks (COFs) is difficult due to stacking issues with chiral units.
  • Helical chirality offers a promising route to control framework assembly and properties.

Purpose of the Study:

  • To introduce helical chirality into 2D COFs using [5]helicene linkers.
  • To investigate the structural, chiroptical, and photoluminescent properties of the resulting [5]HeliCOFs.

Main Methods:

  • Utilized configurationally stable enantiopure and racemic [5]helicenes as building blocks.
  • Employed condensation reactions with 1,3,5-triformylbenzene (TFB) or 1,3,5-triformylphloroglucinol (TFP).
  • Characterized synthesized [5]HeliCOFs as powders and homogeneous thin films.

Main Results:

  • Efficiently formed homochiral and racemic 2D [5]HeliCOFs with distinct structural features.
  • Observed advanced chiroptical properties in the far-red visible spectrum due to propagated helical chirality.
  • Disclosed photoluminescent properties in [5]HeliCOF thin films from ordered π-conjugated lattices.

Conclusions:

  • Successfully integrated helical chirality into 2D COFs, creating [5]HeliCOFs.
  • Demonstrated that helical chirality influences framework structure and optical properties.
  • Extended the Liebisch-Wallach rule to 2D COFs, providing insights into chiral framework formation.