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Fully Collapsed Imploded Cryptophanes in Solution and in the Solid State.

Flora L Thorp-Greenwood1, Mark J Howard1, Lars T Kuhn2

  • 1School of Chemistry, University of Leeds, Leeds, LS2 9JT, UK.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 13, 2019
PubMed
Summary
This summary is machine-generated.

Researchers discovered a novel "out-in" conformation in cryptophanes with flexible linkers. This unique molecular structure, previously uncharacterized, was observed in single crystals and demonstrated dynamic behavior upon heating and cooling.

Keywords:
cage conformationscryptophanesdynamic covalent chemistryhost-guest systemssupramolecular chemistry

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Crystallography

Background:

  • Cryptophanes are cage-like molecules with potential applications in molecular recognition and encapsulation.
  • The conformational behavior of cryptophanes, particularly with flexible linkers, is crucial for understanding their properties.
  • Previous studies have primarily characterized the 'out-out' conformation.

Purpose of the Study:

  • To synthesize and characterize novel cryptophanes with flexible linkers derived from (±)-tris-(4-formyl-phenyl)-cyclotriguaiacylene.
  • To investigate the conformational isomers adopted by these cryptophanes in the solid state.
  • To elucidate the dynamic interconversion between different conformational states.

Main Methods:

  • Single crystal X-ray diffraction analysis to determine molecular structures.
  • Synthesis of cryptophanes utilizing flexible bisoxydi(ethylamine) or bis(aminopropyl)ether linkers.
  • Thermal analysis to study conformational changes upon heating and cooling.

Main Results:

  • Isolation and structural characterization of cryptophanes exhibiting a previously undescribed 'out-in' conformation.
  • In the 'out-in' conformation, cyclotriguaiacylene fragments adopt nested crown conformations.
  • Heating led to the dissolution of crystals and the usual 'out-out' conformation, with a time-dependent reversion to 'out-in' isomers upon cooling.
  • Cryptophanes with rigid dibenzalhydrazine linkers exclusively adopted the 'out-out' conformation.

Conclusions:

  • Flexible linkers enable the formation of a novel 'out-in' cryptophane conformation, distinct from the typical 'out-out' structure.
  • The 'out-in' conformation is a stable, albeit previously uncharacterized, isomer in the solid state.
  • Cryptophane conformation is highly dependent on linker rigidity and can exhibit dynamic behavior.
  • These findings expand the understanding of cryptophane structural diversity and conformational flexibility.