Synthesis and helicate formation of a new family of BINOL-based bis(bipyridine) ligands

Jens Bunzen; Torsten Bruhn; Gerhard Bringmann; Arne Lützen

doi:10.1021/ja807780j

Synthesis and helicate formation of a new family of BINOL-based bis(bipyridine) ligands

J Am Chem Soc. 2009 Mar 18;131(10):3621-30. doi: 10.1021/ja807780j.

Authors

Jens Bunzen¹, Torsten Bruhn, Gerhard Bringmann, Arne Lützen

Affiliation

¹ Kekule-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Strasse 1, D-53121 Bonn, Germany.

PMID: 19231865
DOI: 10.1021/ja807780j

Abstract

A new family of BINOL-based bis(bipyridine) ligands 1-3 (BINOL = 2,2'-dihydroxy-1,1'-binaphthyl) was prepared in enantiomerically pure form. Whereas the coordination of zinc(II) ions to these ligands did not result in the selective formation of a specific metallosupramolecular aggregate, 1-3 were found to undergo highly diastereoselective self-assembly to D(2)-symmetric dinuclear double-stranded helicates upon coordination to silver(I) and copper(I) ions and to D(3)-symmetric dinuclear triple-stranded helicates upon coordination to iron(II) as demonstrated by mass spectrometry and by NMR and CD spectroscopy in combination with quantum chemical calculations.