Oligopyridines

Oligopyridines are planarizable compounds, which are easily accessible, structurally variable, and chemically and thermally stable. The nitrogen atoms provide hydrogen bonding acceptor properties and the molecules could also serve as ligands for complexing metal cations. Thus, this class of compounds is highly versatile.

Molekülstruktur eines Bisterpyridins
Representative example of an oligopyridine (so-called 3,3’-BTP) as highly versatile building block for the construction of self-assembled functional units.

The synthetic approach to the oligopyridines follows ring closure strategies (Kröhnke-type)  which allow precise tailoring of both the periphery and the core structure of the oligomers. Such planar molecules self-assemble easily into two-dimensional monolayers at the solid/liquid and the solid/gas interface. The 2D structures are mainly governed by intermolecular C-HN interactions.

Currently we are mainly interested in functionalizing the periphery with clickable groups to connect the pyridine moiety to biologically relevant molecules like peptides and provoke defined arrays of the latter by synthetic self-assembly processes.

  • Ziener, U.; Lehn, J.-M.; Mourran, A.; Möller, M. Supramolecular Assemblies of a Bis(terpyridine) Ligand and of its [2x2] Grid-type ZnII and CoII Complexes on Highly Ordered Pyrolytic Graphite. Chem.-Eur. J. 2002, 8 (4), 951.
  • Meier, C.; Ziener, U.; Landfester, K.; Weihrich, P. Weak Hydrogen Bonds as a Structural Motif for Two-Dimensional Assemblies of Oligopyridines on Highly Oriented Pyrolytic Graphite: An STM Investigation. J. Phys. Chem. B 2005, 109 (44), 21015.
  • Ziener, U. Self-Assembled Nanostructures of Oligopyridine Molecules. J. Phys. Chem. B 2008, 112 (47), 14698.
  • Meier, C.; Landfester, K.; Künzel, D.; Markert, T.; Groß, A.; Ziener, U. “Hierarchically Self-Assembled Host-Guest Network at the Solid/Liquid-Interface for Single Molecule Manipulation”, Angew. Chem. 2008, 120(20), 3881-3885.    
  • Meier, C.; Roos, M.; Künzel, D.; Breitruck, A.; Hoster, H.; Landfester, K.; Gross, A.; Behm, R. J.; Ziener, U. Concentration and Coverage Dependent Adlayer Structures: From Two-dimensional Networks to Rotation in a Bearing. J. Phys. Chem. C 2010, 114 (2), 1268.
  • Dai, Y.; Metzler, M.; Jacob, T.; Kolb, D. M.; Ziener, U. Fast vs. Slow: Electrolyte and Potential Dependent Adlayer Switching of an Oligopyridine on Au(111). Electrochim. Acta 2014, 137 (0), 416.