Self-sorting among the diastereoisomers of a M₃L₂ subphthalocyanine capsule

Abstract

A new M₃L₂ homodimeric subphthalocyanine cage was self-assembled and characterised. Among the six possible diastereoisomeric metallosupramolecular capsules attainable, only one was shown to form under thermodynamic conditions. These results obtained on the basis of mass spectrometry, nuclear magnetic resonance and molecular modelling studies demonstrate that dynamic chiral self-discrimination occurs when the cage compound is left enough time to reach equilibrium.

Keywords:

• subphthalocyanines
• palladium complexes
• capsules
• metallosupramolecular chemistry
• chiral self-discrimination

Acknowledgements

Financial support from the Ministerio de Ciencia y Tecnología (CTQ2005-08933/BQU and Consolider-Ingenio 2010 CSD2006-0015), Comunidad de Madrid (MADRISOLAR, S-0505/PPQ/0225) and EU (MRTN-CT-2006-035533, Solar-N-type) is gratefully acknowledged.