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Self‐Sorting Effects in the Self‐Assembly of Metallosupramolecular Rhombi from Chiral BINOL‐Derived Bis(pyridine) Ligands
Author(s) -
Gütz Christoph,
Hovorka Rainer,
Stobe Caroline,
Struch Niklas,
Topić Filip,
Schnakenburg Gregor,
Rissanen Kari,
Lützen Arne
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301314
Subject(s) - chemistry , enantiopure drug , self assembly , stereochemistry , steric effects , pyridine , enantioselective synthesis , ligand (biochemistry) , crystallography , medicinal chemistry , organic chemistry , catalysis , biochemistry , receptor
Abstract Four BINOL‐based bis(4‐pyridyl) ligands were synthesised in enantiopure and racemic form. These ligands form metallosupramolecular [(dppp) 2 M 2 L 2 ] rhombi with cis ‐protected [(dppp)Pd] 2+ and [(dppp)Pt] 2+ ions. In principle, racemic ligands can self‐assemble into three stereoisomeric rhombi. The degree of self‐sorting in the self‐assembly process crucially depends on the substitution pattern and the resulting bend angle of the V‐shaped ligands as well as the degree of steric crowding within the assembly when racemic ligands are used. Thus, these processes either lead to homochiral assemblies in a narcissistic self‐recognition manner, to heterochiral assemblies in a social self‐discriminating manner, or proceed in a nonselective fashion as evidenced by NMR spectroscopy, mass spectrometry and single‐crystal X‐ray diffraction.

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