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Tunable Fullerene Affinity of Cages, Bowls and Rings Assembled by Pd II Coordination Sphere Engineering
Author(s) -
Chen Bin,
Horiuchi Shinnosuke,
Holstein Julian J.,
Tessarolo Jacopo,
Clever Guido H.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201903317
Subject(s) - steric effects , quinoline , chemistry , acridine , pyridine , fullerene , crystallography , ligand (biochemistry) , denticity , benzene , stereochemistry , crystal structure , medicinal chemistry , organic chemistry , biochemistry , receptor
For metal‐mediated host compounds, the development of strategies to reduce symmetry and introduce multiple functionalities in a non‐statistical way is a challenging task. We show that the introduction of steric stress around the coordination environment of square‐planar Pd II cations and bis‐monodentate nitrogen donor ligands allows to control the size and shape of the assembled product, from [Pd 2 L 4 ] cages over [Pd 2 L 3 ] bowl‐shaped structures to [Pd 2 L 2 ] rings. Therefore, banana‐shaped ligand backbones were equipped with pyridines, two different quinoline isomers and acridine, the latter three introducing steric congestion through hydrogen substituents on annelated benzene rings. Differing behavior of the four resulting hosts towards the binding of C 60 and C 70 fullerenes was studied and related to structural differences by NMR spectroscopy, mass spectrometry and single crystal X‐ray diffraction. The three cages based on pyridine, 6‐quinoline or 3‐quinoline donors were found to either bind C 60 , C 70 or no fullerene at all.