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Axially Chiral Spiro Compounds with Heavier Group 14 Elements as Spiro-Centers.

Aynura Mammadova1, Clemens Bruhn1, Rudolf Pietschnig1

  • 1Institute for Chemistry and CINSaT, University of Kassel, Heinrich-Plett-Straße 40, Kassel 34132, Germany.

Inorganic Chemistry
|May 2, 2026
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Summary
This summary is machine-generated.

New chiral ligands featuring tert-butyl groups were synthesized and used to create novel axially chiral compounds with Group 14 elements. Researchers explored their structural properties and reactivity, particularly with lead and germanium complexes.

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Area of Science:

  • Organometallic Chemistry
  • Ligand Synthesis
  • Chiral Chemistry

Background:

  • Development of novel ditopic ligands is crucial for creating new organometallic compounds.
  • Axially chiral molecules with Group 14 elements are of interest due to their unique properties and potential applications.
  • The synthesis and characterization of ligands with thiol and selenol groups offer versatile coordination possibilities.

Purpose of the Study:

  • To prepare homo- and heteroditopic 4-tert-butyl-1,2-benzene-bischalcogenol ligands.
  • To synthesize and characterize novel axially chiral compounds incorporating Group 14 elements (Sn, Ge, Pb).
  • To investigate the reactivity and aggregation behavior of the synthesized complexes, especially lead derivatives.

Main Methods:

  • Functionalization of 4-tert-butylthiophenol to introduce thiol and selenol groups.
  • Isolation and structural characterization of lithiated ligand derivatives.
  • Synthesis of Group 14 complexes and their characterization using multinuclear NMR spectroscopy, elemental analysis (EA), high-resolution mass spectrometry (HR-MS), and single-crystal X-ray diffraction (SCXRD).
  • Exploration of chiral resolution using high-performance liquid chromatography (HPLC) for germanium compounds.

Main Results:

  • Successfully synthesized and characterized novel homo- and heteroditopic bis(chalcogenol) ligands.
  • Prepared axially chiral complexes of tin, germanium, and lead.
  • Observed reduction of Pb(IV) to Pb(II) in lead complexes, leading to aggregation; adducts were formed with donor molecules but did not deaggregate the polymeric structure.
  • Stable germanium complexes were synthesized, and attempts at chiral resolution via HPLC were explored.

Conclusions:

  • The developed ligands are versatile precursors for synthesizing novel axially chiral organometallic compounds.
  • The reactivity of lead complexes differs significantly, showing a tendency towards reduction and aggregation.
  • The synthesized germanium compounds represent stable chiral frameworks with potential for further investigation and resolution.