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The Influence of Different Spacer Lengths on the Selectivity of Self‐Assembly Processes of Bis(bipyridine)‐BINOL Helicates
Author(s) -
Bunzen Jens,
Hapke Marko,
Lützen Arne
Publication year - 2009
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.200900232
Subject(s) - chemistry , chelation , zinc , bipyridine , self assembly , stereochemistry , selectivity , nuclear magnetic resonance spectroscopy , polymer chemistry , medicinal chemistry , crystallography , organic chemistry , catalysis , crystal structure
The synthesis and self‐assembly behaviour of a series of enantiomerically pure bis(chelating) ligands is reported. The ligands differ in the spacer unit between a BINOL core and two bipyridyl groups as the chelating entities and were found to undergo completely diastereoselective self‐assembly to dinuclear double‐stranded helicates with silver(I) salts, as demonstrated by NMR and CD spectroscopy and ESI mass spectrometry. Upon coordination to iron(II) or zinc(II) ions, however, a dramatic loss in the diastereoselectivity of the self‐assembly of dinuclear triple‐stranded helicates was observed as a result of increasing spacer length. In the case of zinc(II), the self‐assembly processes were even found to be nonselective with regard to the composition of the helicates.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)