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Solvent-Directed Social Chiral Self-Sorting in Pd2L4 Coordination Cages.

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Chiral ligands form Pd2L4 cages. Solvent molecules drive self-sorting in shorter ligands, yielding a single meso-trans cage isomer through hydrogen bonding. Longer ligands do not self-sort but form cages that bind metal complexes and discriminate enantiomers.

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Area of Science:

  • Supramolecular Chemistry
  • Coordination Chemistry
  • Organic Synthesis

Background:

  • Axially chiral diamino-[1,1'-biazulene] ligands serve as azulene-based surrogates for BINOL.
  • Coordination cages offer tunable cavities for molecular recognition and catalysis.

Purpose of the Study:

  • To investigate the formation of Pd2L4 cages using novel biazulene-based ligands.
  • To explore the phenomenon of "social" chiral self-sorting in coordination cage assembly.
  • To understand the role of solvents in directing the stereochemical outcome of cage formation.

Main Methods:

  • Synthesis of axially chiral diamino-[1,1'-biazulene] ligands with pyridine and isoquinoline donors.
  • Preparation of Pd2L4 coordination cages via self-assembly.
  • Characterization using NMR spectroscopy and single-crystal X-ray diffraction.
  • Computational analysis including explicit solvation models.

Main Results:

  • A shorter biazulene ligand derivative undergoes solvent-dependent "social" chiral self-sorting from its racemate, exclusively forming the meso-trans Pd2L4 cage.
  • Solvent molecules act as hydrogen-bonding tethers, locking the cage into a single isomeric form.
  • A larger biazulene ligand derivative does not exhibit social self-sorting but forms homochiral cages capable of binding metal complexes and discriminating enantiomers.

Conclusions:

  • Solvent-mediated hydrogen bonding is crucial for achieving selective chiral self-sorting in the assembly of specific coordination cages.
  • The size and donor groups of chiral ligands significantly influence their self-sorting behavior.
  • The developed biazulene-based cages demonstrate potential for host-guest chemistry and enantioselective recognition.