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Directing the Solid-State Organization of Racemates via Structural Mutation and Solution-State Assembly Processes.

Chidambar Kulkarni1, José Augusto Berrocal1, Martin Lutz2

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Controlling molecular assembly, even for mixtures of enantiomers (racemates), is challenging. This study shows subtle structural changes and understanding solution assembly can rationally control solid-state organization for trans-1,2-disubstituted cyclohexanes.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Chirality is crucial for biomolecular recognition and drug activity.
  • Controlling the assembly of enantiopure systems is advanced, but racemates remain challenging.
  • Rational control over molecular organization is key for advanced material properties.

Purpose of the Study:

  • To demonstrate rational control over the solid-state assembly of racemates.
  • To investigate the relationship between solution-phase assembly and solid-state organization.
  • To explore the assembly behavior of trans-1,2-disubstituted cyclohexanes with varying functional groups.

Main Methods:

  • Studied trans-1,2-disubstituted cyclohexanes with carboxamide, thioamide, and combined functional groups.
  • Compared gelation propensity of individual enantiomers and racemates in dilute solution and concentrated gels.
  • Analyzed assembly modes including self-sorting, coassembly, and mixed organization.

Main Results:

  • Racemates of carboxamide, thioamide, and their combination exhibited distinct assembly modes: self-sorting, coassembly, and mixed organization, respectively.
  • These solution-phase assembly behaviors were successfully retained in the solid-state.
  • Subtle molecular structure changes influenced the assembly pathways.

Conclusions:

  • Solution-phase assembly studies provide a critical link to understanding and controlling solid-state molecular organization, even for racemates.
  • Rational control of supramolecular structures is achievable by understanding enantiomer and racemate assembly.
  • This work offers a pathway to design solid-state materials with predictable organization from molecular mixtures.