Subcomponent Self-Assembly of a Cyclic Tetranuclear FeII Helicate in a Highly Diastereoselective Self-Sorting Manner |
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Authors: | Jana Anhäuser Dr Rakesh Puttreddy Lukas Glanz Andreas Schneider Dr Marianne Engeser Prof?Dr Kari Rissanen Prof?Dr Arne Lützen |
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Institution: | 1. Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Strasse1, 53121 Bonn, Germany;2. Department of Chemistry, University of Jyväskylä, P.O. Box 35, 40014 Jyväskylä, Finland |
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Abstract: | An enantiomerically pure diamine based on the 4,15-difunctionalized 2.2]paracyclophane scaffold and 2-formylpyridine self-assemble into an optically pure cyclic metallosupramolecular Fe4L6 helicate upon mixing with iron(II) ions in a diastereoselective subcomponent self-assembly process. The cyclic assembly results from steric strain that prevents the formation of a smaller linear dinuclear triple-stranded helicate, and hence, leads to the larger strain-free assembly that fulfils the maximum occupancy rule. Interestingly, use of the racemic diamine also leads to a racemic mixture of the homochiral cyclic helicates as the major product in a highly diastereoselective narcissistic chiral self-sorting manner given the fact that the assembly contains ten stereogenic elements, which can in principle give rise to 149 different diastereomers. The metallosupramolecular aggregates could be characterized by NMR, UV/Vis and CD spectroscopy, mass spectrometry, and X-ray crystallography. |
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Keywords: | chiral self-sorting cyclic helicates paracyclophanes self-assembly supramolecular chemistry |
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