Synthesis, Chiral Resolution, and Absolute Configuration of Functionalized Tröger’s Base Derivatives: Part III

An ew bis(salicylimine)l igand based on the Trç-ger's base scaffold was synthesized in racemic and enantiomerically pure form. Upon coordinationt oz inc(II) ions this ligand undergoes highly diastereoselective self-assembly into neutral dinuclear double-stranded helicates as proven by XRD analysisa nd via comparison of experimental ECD spectra with those simulated with quantum-chemicalm ethods. When the racemic ligand was used, self-assembly occurs under narcissistic self-sorting resulting in the formation of ar acemic pair of helicates as revealed by NMR spectroscopya nd XRD analysis.

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Diastereoselective Self‐Assembly of a Neutral Dinuclear Double‐Stranded Zinc(II) Helicate via Narcissistic Self‐Sorting

Jarzebski

Tenten

Bannwarth

et al. 2017

Chemistry A European J

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ChemInform Abstract: Synthesis, Chiral Resolution, and Absolute Configuration of Functionalized Troeger′s Base Derivatives: Part 3

Jarzebski¹,

Bannwarth²,

Tenten³

et al. 2015

ChemInform

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Chiral Self‐Sorting Effects in the Self‐Assembly of Metallosupramolecular Aggregates Comprising Ligands Derived from Tröger's Base

2020

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Five ligands with either nitrile or isonitrile metal binding motifs have been synthesized based on the 2,8‐ or 3,9‐disubstituted Tröger's base scaffold, respectively. These ligands self‐assemble into dinuclear cyclic metallosupramolecular aggregates upon coordination to [(dppp)Pd(OTf)2] in a highly diastereoselective manner, by heterochiral self‐sorting in a chiral self‐discriminating manner as shown by ESI mass spectrometry, NMR spectroscopy, and single crystal XRD analysis. This observation is in contrast to earlier studies with ligands derived from Tröger's base that have larger metal binding motifs and bis(nitrile) and bis(isonitrile) ligands based on other rigid dissymmetric cores such as [2.2]paracyclophanes. Thus, the combination of these slim metal binding motifs with the rigid v‐shaped 2,8‐ or 3,9‐disubstituted Tröger's base scaffolds seems to be especially well preorganized to ensure high‐fidelity social self‐sorting behavior.

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Synthesis, Chiral Resolution, and Absolute Configuration of Functionalized Tröger’s Base Derivatives: Part III

Cited by 9 publications

References 7 publications

Diastereoselective Self‐Assembly of a Neutral Dinuclear Double‐Stranded Zinc(II) Helicate via Narcissistic Self‐Sorting

Diastereoselective Self‐Assembly of a Neutral Dinuclear Double‐Stranded Zinc(II) Helicate via Narcissistic Self‐Sorting

ChemInform Abstract: Synthesis, Chiral Resolution, and Absolute Configuration of Functionalized Troeger′s Base Derivatives: Part 3

Chiral Self‐Sorting Effects in the Self‐Assembly of Metallosupramolecular Aggregates Comprising Ligands Derived from Tröger's Base

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