Self-Discriminating Self-Assembly of Dinuclear Heterochiral Rhombs from Tröger's Base Derived Bis(pyridyl) Ligands

Five racemic dissymmetric bis(pyridyl) ligands based on 2,8‐ or 3,9‐difunctionalised Tröger’s base derivatives have been synthesised. Only those derived from a 2,8‐difunctionalised scaffold were found to undergo selective self‐assembly to discrete self‐assembled dinuclear metallosupramolecular aggre...

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Bibliographic Details
Published in:Chemistry : a European journal 2010-02, Vol.16 (8), p.2418-2426
Main Authors: Weilandt, Torsten, Kiehne, Ulf, Bunzen, Jens, Schnakenburg, Gregor, Lützen, Arne
Format: Article
Language:English
Subjects:
Aggregates
Bearing
Chemistry
diastereoselectivity
Ligands
palladium
platinum
Scaffolds
Self assembly
supramolecular chemistry
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Summary:Five racemic dissymmetric bis(pyridyl) ligands based on 2,8‐ or 3,9‐difunctionalised Tröger’s base derivatives have been synthesised. Only those derived from a 2,8‐difunctionalised scaffold were found to undergo selective self‐assembly to discrete self‐assembled dinuclear metallosupramolecular aggregates of rhomboid shape upon coordination to cis‐protected Pd2+ or Pt2+ ions, as evidenced by ESI mass spectrometry, NMR spectroscopy and single‐crystal X‐ray diffraction. Interestingly, these processes were found to be highly diastereoselective leading to the formation of C2v‐symmetric heterochiral assemblies in a self‐discriminating manner. Diastereoselective self‐assembly: Bis(pyridyl) ligands bearing a 2,8‐disubstituted Tröger's base scaffold undergo diastereoselective self‐assembly to yield discrete dinuclear achiral metallosupramolecular rhombs upon coordination to cis‐protected palladium(II) or platinum(II) ions in a self‐discriminating manner (see figure), whereas their analogues with a 3,9‐disubstituted Tröger's base core do not even assemble selectively in terms of aggregate composition.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.200902993