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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Organic Chemistry

Background:

  • Self-assembly of molecular components into ordered structures is crucial for developing advanced materials.
  • Chirality plays a significant role in dictating the properties of supramolecular assemblies.
  • Organogelation is a promising method for creating responsive materials with tunable characteristics.

Purpose of the Study:

  • To investigate the formation of double helical structures from optically active amidine and achiral carboxylic acid dimers.
  • To explore the gelation behavior of these duplexes in response to solvent polarity.
  • To analyze the chiroptical properties and chirality amplification during the organogelation process.

Main Methods:

  • Synthesis of optically active amidine and achiral carboxylic acid dimers with specific backbones and linkers.
  • Formation of double helical duplexes through amidinium-carboxylate salt bridges in tetrahydrofuran (THF).
  • Induction of organogelation by adding poor solvents like n-hexane.
  • Characterization using absorption spectroscopy and circular dichroism (CD) spectroscopy.

Main Results:

  • Optically active amidine-carboxylic acid duplexes formed double helices and subsequently organogels upon addition of poor solvents.
  • Gelation was attributed to supramolecular polymerization driven by intermolecular salt bridge rearrangement.
  • A contrasting lack of gelation was observed for a racemic duplex or a duplex with a shorter, higher-affinity linker, highlighting structural sensitivity.
  • The resulting supramolecular fluorescent gels demonstrated reversible thermo- and chemoresponsive behavior.
  • Chiroptical properties and chirality amplification were observed during gelation, with variations depending on the presence of enantiomers or racemic mixtures.

Conclusions:

  • Specific structural and chiral features of molecular dimers are essential for the formation of double helical structures and subsequent organogelation.
  • The process of supramolecular polymerization via salt bridge rearrangement is a key mechanism for organogel formation in this system.
  • The study demonstrates the potential for designing responsive supramolecular materials with amplified chirality.