Rigid p-conjugated 2,2':6',2''-terpyridines: Synthesis and potential applications

ORGN 288

Andreas Winter, a.winter@tue.nl1, Florian Schlütter, florian.schluetter@uni-jena.de2, Ronald Siebert3, Andreas Wild, andy.wild@uni-jena.de2, Christian Friebe, christian.friebe@uni-jena.de2, Martin D. Hager, martin.hager@uni-jena.de2, Benjamin Dietzek, benjamin.dietzek@uni-jena.de4, Michael Schmitt3, Jürgen Popp4, and Ulrich S. Schubert, ulrich.schubert@uni-jena.de2. (1) Laboratory of Macromolecular Chemistry and Nanoscience, Eindhoven University of Technology and Dutch Polymer Institute, P.O. Box 513, Eindhoven, 5600 MB, Netherlands, (2) Laboratory of Organic and Macromolecular Chemistry, Friedrich-Schiller-University Jena, Humboldtstr. 10, Jena, 07743, Germany, (3) Insitute of Physical Chemistry, Friedrich-Schiller-University Jena, Helmholtzweg 4, Jena, 07743, Germany, (4) Insitute of Physical Chemistry, Friedrich-Schiller-University Jena and Insitute of Photonic Technology, Helmholtzweg 4, Jena, 07743, Germany
The self-assembly of functional structures into metallo-supramolecular architectures through the interaction of transition metal ions and appropriate ligands is a highly active area in modern supramolecular chemistry. Bringing together the chemistry of terpyridines, as well as their transition metal complexes, and of p-conjugated polymers, we here present the synthesis of a diverse library of rigid p-conjugated oligo(terpyridine)s. Highly effective combinations of well-known condensation reactions and modern transition metal-catalyzed coupling reactions enable us to synthesize tailor-made terpyridine-derivatives with respect to their photophysical properties. The electro-optical properties of all materials have been studied in solution and in the solid state. Additionally, we show examples for the complexation of the p-conjugated oligo(terpyridine)s with various transition metal ions leading to various types of supramolecular assemblies (e.g. ABA-block copolymers, chain-extended polymers and PPE/PPV-type oligomers) and potential applications in the fields of photovoltaics or organic light-emitting devices.


Heterocycles and Aromatics
1:00 PM-5:20 PM, Monday, August 17, 2009 Walter E. Washington Convention Center -- 206, Oral

Division of Organic Chemistry

The 238th ACS National Meeting, Washington, DC, August 16-20, 2009