Project A8: Organic Molecular Building Blocks for the Synthesis of Internal Interfaces

Principle Investigator: Prof. Dr. Ulrich Koert (Marburg, Dept. of Chemistry), Prof. Dr. Michael Dürr (Gießen, Inst. of Appl. Physics)

Summary

The central aim of this project is the chemical synthesis of organic molecules which are employed for building organic-inorganic internal interfaces of highest quality for further investigation within the CRC. The contact of the organic phase to the inorganic/semiconductor interface is intended via aromatic π-interaction or by covalent bonding (e.g. cycloaddition).
In part A novel fluoro-substituted (aza)pentacene and DNTT derivatives will be synthesized and their packing motif will be characterized by X-ray analysis. Organic-[inorganic/semiconductor] interfaces prepared from the novel (aza)pentacenes and DNTTs will be characterized in collaboration with the physics groups.
In part B, well-ordered multilayers will be generated on Si(001). Based on the chemoselective reactivity of functionalized cyclooctynes on Si(001) as demonstrated in the first funding period, second and third layer attachment will be realized employing azide/alkyne reactions.

Project-related publications

1. F. Wagner, K. Harms, U. Koert Hauser-Heck: Efficient Synthesis of γ-Aryl-β-Ketoesters en route to substituted Naphthalenes Org. Lett. 17, 5670 (2015).
2. J. Schwaben, N. Münster, M. Klues, T. Breuer, P. Hofmann, K. Harms, G. Witte, U. Koert Efficient Syntheses of Novel Fluoro-Substituted Pentacenes and Azapentacenes: Molecular and Solid-State Properties Chem. Eur. J. 21, 13758 (2015).
3. N. Münster, P. Nikodemiak, U. Koert A Chemoselective Layer-by-Layer Approach Utilizing Click-Reactions with Ethynyl-cyclooctynes and Diazides Org. Lett. 18, 4296 (2016).
4. M. Reutzel, N. Münster, M. Lipponer, C. Länger, U, Höfer, U. Koert, M. Dürr Chemoselective Reactivity of Bifunctional Cyclooctynes on Si(001) J. Phys. Chem. C, 120, 26284 (2016).