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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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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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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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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.
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A Multiresponsive Ferrocene-Based Chiral Overcrowded Alkene Twisting Liquid Crystals.

Maximilian Fellert1, Robert Hein1, Alexander Ryabchun1

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Summary

Researchers developed a novel chiral switch (FcD) from ferrocene-indanone building blocks. This switch exhibits multi-stimuli responsiveness, enabling significant tuning of liquid crystal properties through redox and isomerization.

Keywords:
Asymmetric synthesisFerroceneLiquid crystalsMolecular SwitchRedox chemistry

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Organic Synthesis

Background:

  • Reversible chirality modulation is crucial for advanced applications like liquid crystals (LCs) and molecular machines.
  • Synthesizing enantioselective, switchable molecules with multiple chiral elements presents significant challenges.

Purpose of the Study:

  • To develop a novel, easily synthesized, multi-stimuli-responsive chiral switch.
  • To investigate the switchable (chir)optical properties of the synthesized molecule.
  • To explore its application as a chiral dopant in cholesteric liquid crystals.

Main Methods:

  • Stereoselective dimerization of an enantiopure planar chiral ferrocene-indanone building block.
  • Characterization of the resulting dimer (FcD) for its structural and stereochemical properties.
  • Investigation of thermal/photochemical E/Z isomerization and reversible redox behavior (mono- and di-cationic states).
  • Evaluation of FcD as a chiral dopant in cholesteric liquid crystals and its response to oxidation.

Main Results:

  • High-yield synthesis of the multi-stimuli-responsive dimer (FcD) with controlled geometry and chirality.
  • FcD exhibits reversible thermal/photochemical E/Z isomerization and tunable redox states.
  • FcD functions as a chiral dopant in LCs with a helical twisting power (HTP) of 13 μm⁻¹, which drops to near zero upon oxidation.
  • Oxidation induces a significant redox-tuning of LC reflection color by up to 84 nm.

Conclusions:

  • The straightforward synthesis of FcD makes it a promising building block for advanced molecular machines.
  • FcD offers unprecedented redox-tuning capabilities for liquid crystal-based materials.
  • This work provides a new platform for designing multi-stimuli-responsive chiral materials.