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Issue 8, 2019
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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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Article information


Submitted
29 Jan 2019
Accepted
11 Mar 2019
First published
12 Mar 2019

Org. Chem. Front., 2019,6, 1226-1235
Article type
Research Article

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, 6, 1226
DOI: 10.1039/C9QO00155G

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