Equipping metallo-supramolecular macrocycles with functional groups: assemblies of pyridine-substituted urea ligands

A series of di-(m-pyridyl)-urea ligands were prepared and characterized with respect to their conformations by NOESY experiments and crystallography. Methyl substitution in different positions of the pyridine rings provides control over the position of the pyridine N atoms relative to the urea carbo...

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Bibliographic Details
Published in:Dalton transactions : an international journal of inorganic chemistry 2012-07, Vol.41 (27), p.8410-8420
Main Authors: Troff, Ralf W, Hovorka, Rainer, Weilandt, Torsten, Lützen, Arne, Cetina, Mario, Nieger, Martin, Lentz, Dieter, Rissanen, Kari, Schalley, Christoph A
Format: Article
Language:English
Subjects:
Assemblies
Carbonyl groups
Crystallography
Hydrogen bonding
Ligands
Macrocyclic compounds
Pyridines
Rings (mathematics)
Ureas
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Summary:A series of di-(m-pyridyl)-urea ligands were prepared and characterized with respect to their conformations by NOESY experiments and crystallography. Methyl substitution in different positions of the pyridine rings provides control over the position of the pyridine N atoms relative to the urea carbonyl group. The ligands were used to self-assemble metallo-supramolecular M(2)L(2) and M(3)L(3) macrocycles which are generated in a finely balanced equilibrium in DMSO and DMF according to DOSY NMR experiments and ESI FTICR mass spectrometry. Again, crystallography was used to characterize the assemblies. Methyl substitution in positions next to the pyridine nitrogen prevents coordination, while the other ligands form small metallo-supramolecular macrocycles. The incorporated urea carbonyl groups provide hydrogen bonding sites which converge towards the center of the assemblies.
ISSN:1477-9226
1477-9234
DOI:10.1039/c2dt30190c