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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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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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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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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.
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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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Isomerism in Complexes
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Related Experiment Video

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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Axially chiral BODIPYs.

Reinner I Lerrick1, Thomas P L Winstanley, Karen Haggerty

  • 1School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU, UK. m.hall@ncl.ac.uk.

Chemical Communications (Cambridge, England)
|March 29, 2014
PubMed
Summary

Researchers synthesized and resolved novel axially chiral 4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes (Ax*-BODIPY) organic fluorophores. These chiral BODIPY derivatives were created using modular synthesis and Heck functionalization, with stereochemistry confirmed by ECD spectroscopy.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Spectroscopy

Background:

  • Chiral organic fluorophores are crucial for advanced optical and electronic applications.
  • Developing new chiral molecules with tunable properties remains a significant challenge.
  • Axially chiral BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) scaffolds offer unique photophysical characteristics.

Purpose of the Study:

  • To describe the synthesis and resolution of a novel class of axially chiral BODIPY derivatives (Ax*-BODIPYs).
  • To establish a modular synthetic route for creating these chiral fluorophores.
  • To determine the absolute stereochemistry of the synthesized compounds.

Main Methods:

  • Modular synthesis approach.
  • Late-stage Heck functionalization for structural elaboration.
  • Preparative chiral High-Performance Liquid Chromatography (HPLC) for enantiomeric separation.
  • Electronic Circular Dichroism (ECD) spectroscopy.
  • Time-Dependent Density-Functional Theory (TD-DFT) calculations for stereochemical assignment.

Main Results:

  • Successful synthesis of axially chiral Ax*-BODIPYs.
  • Efficient separation of enantiomers using chiral HPLC.
  • Determination of absolute stereochemistry through comparison of experimental ECD spectra and TD-DFT computed spectra.
  • Demonstration of a versatile synthetic strategy for chiral BODIPY construction.

Conclusions:

  • A robust method for synthesizing and resolving chiral Ax*-BODIPYs has been developed.
  • The established methodology enables access to enantiomerically pure chiral BODIPY fluorophores.
  • This work expands the toolkit for creating chiral organic materials with potential applications in asymmetric catalysis, sensing, and imaging.