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Chiral self-sorting behaviour of [2.2]paracyclophane-based bis(pyridine) ligands

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Abstract

Two constitutionally isomeric chiral bis(pyridine) ligands based on planar chiral 4,15-difunctionalized [2.2]paracyclophanes were synthesized, the respective enantiomers were separated via HPLC on a chiral stationary phase, and their self-assembly behaviour upon coordination to palladium(II) ions was studied with regard to chiral self-sorting effects. As proven by NMR spectroscopy, mass spectrometry, CD spectroscopy, UV-Vis spectroscopy and X-ray crystallography both ligands form the expected dinuclear complexes upon coordination to cis-protected di- or tetravalent palladium(II) ions, respectively, however, with distinct differences concerning their chiral self-sorting ability.

Graphical abstract: Chiral self-sorting behaviour of [2.2]paracyclophane-based bis(pyridine) ligands

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Publication details

The article was received on 29 Jan 2019, accepted on 11 Mar 2019 and first published on 12 Mar 2019


Article type: Research Article
DOI: 10.1039/C9QO00155G
Citation: Org. Chem. Front., 2019, Advance Article

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    Chiral self-sorting behaviour of [2.2]paracyclophane-based bis(pyridine) ligands

    J. Anhäuser, R. Puttreddy, Y. Lorenz, A. Schneider, M. Engeser, K. Rissanen and A. Lützen, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00155G

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