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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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Chiral Spiro-Tetrathiafulvalenes: Synthesis, Chiroptical Properties, Conformational Issues and Charge Transfer

Alexandra Bogdan1,2, Ionut-Tudor Moraru3, Nicolas Vanthuyne4

  • 1Univ Angers, CNRS, MOLTECH-Anjou, SFR MATRIX, F-, 49000, Angers, France.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 25, 2024
PubMed
Summary

This study separated and characterized stereoisomers of spiro-based tetrathiafulvalenes (TTFs). These chiral TTFs were then used to synthesize novel charge transfer complexes with tetracyanoquinodimethane (TCNQ) acceptors.

Keywords:
TD-DFT calculationschiralitycircular dichroismspiro compoundstetrathiafulvalene

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Area of Science:

  • Organic Chemistry
  • Stereochemistry
  • Materials Science

Background:

  • Spiro-based tetrathiafulvalenes (TTFs) are valuable organic molecules.
  • Previous studies lacked detailed stereoisomer separation and characterization.
  • Understanding stereoisomer-specific properties is crucial for advanced applications.

Purpose of the Study:

  • To separate and fully characterize stereoisomers of spiro-based TTFs.
  • To investigate the relationship between molecular structure and optical activity.
  • To explore the synthesis of charge transfer complexes using these chiral TTFs.

Main Methods:

  • Synthesis of spiro-based TTFs from racemic spiro[5.5]undeca-1,8-dien-3-one.
  • Separation of enantiomeric and diastereoisomeric forms using chiral High-Performance Liquid Chromatography (HPLC).
  • Comprehensive experimental and theoretical characterization, including Circular Dichroism (CD) spectroscopy and Time-Dependent Density-Functional Theory (TD-DFT) calculations.

Main Results:

  • Successful separation and characterization of distinct stereoisomers (1, 2, 3, and 5) of spiro-TTFs.
  • Experimental CD spectra, supported by TD-DFT, revealed differences in optical activity correlating with the number and type of chiral centers.
  • Optical activity in derivatives with spiro chirality alone was attributed to conformational equilibria, while derivatives with additional stereogenic centers showed contributions from both spiro and stereogenic chiralities.

Conclusions:

  • Stereoisomers of spiro-based TTFs can be effectively separated and characterized.
  • The study provides insights into the origin of optical activity in chiral spirocyclic systems.
  • Racemic and enantiopure spiro-TTFs serve as effective building blocks for charge transfer complexes with tetracyanoquinodimethane (TCNQ) acceptors.