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Pentameric Circular Iron(II) Double Helicates and a Molecular Pentafoil Knot

DOI: 10.1021/ja303355v DOI Help
PMID: 22554153 PMID Help

Authors: Jean-françois Ayme (University of Edinburgh) , Jonathon E. Beves (University of Edinburgh) , David Leigh (University of Manchester; University of Edinburgh) , Roy T. Mcburney (University of Edinburgh) , Kari Rissanen (University of Jyväskylä) , David Schultz (University of Edinburgh)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Journal Of The American Chemical Society , VOL 134 , PAGES 9488 - 9497

State: Published (Approved)
Published: June 2012
Diamond Proposal Number(s): 029

Abstract: We report on the synthesis of II pentameric cyclic helicates formed by imine condensation of alkyl monoamines with a common bis(formylpyridine)-bipyridyl-derived building block and iron(II) and chloride ions. The cyclic double-stranded helicates were characterized by NMR spectroscopy, mass spectrometry, and in the case of a 2,4-dimethoxybenzylamine-derived pentameric cyclic helicate, X-ray crystallography. The factors influencing the assembly process (reactant stoichiometry, concentration, solvent, nature and amount of anion) were studied in detail: the role of chloride in the assembly process appears not to be limited to that of a simple template, and larger circular helicates observed with related tris(bipyridine) ligands with different iron salts are not produced with the imine ligands. Using certain chiral amines, pentameric cyclic helices of single handedness could be isolated and the stereochemistry of the helix determined by circular dichroism. By employing a particular diamine, a closed-loop molecular pentafoil knot was prepared. The pentafoil knot was characterized by NMR spectroscopy, mass spectrometry, and X-ray crystallography, confirming the topology and providing insights into the reasons for its formation.

Subject Areas: Chemistry

Instruments: I19-Small Molecule Single Crystal Diffraction

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