Bereiche | Tage | Auswahl | Suche | Aktualisierungen | Downloads | Hilfe

O: Fachverband Oberflächenphysik

O 77: Organic Molecules on Inorganic Substrates V: Solid-Liquid Interfaces, Self-Organization, Ordering

O 77.10: Vortrag

Donnerstag, 4. April 2019, 12:45–13:00, H9

Formation of Si/organic interfaces using alkyne-functionalized cyclooctynes — Christian Länger¹, •Julian Heep¹, Paul Nikodemiak², Tamam Bohamud², Patrick Kirsten¹, Ulrich Höfer², Ulrich Koert², and Michael Dürr¹ — ¹Justus-Liebig-Universität, 35392 Gießen — ²Philipps-Universität, 35037 Marburg

Controlled organic functionalization of semiconductor surfaces requires chemoselective adsorption of bifunctional molecules on the surface. Here we show for ethynyl-cyclopropyl-cyclooctyne (ECCO), an alkyne-functionalized cyclooctyne, that such chemoselective adsorption can be achieved on Si(001) despite the high reactivity of both functional groups in the molecule, i.e., the strained triple bond of cyclooctyne and the terminal triple bond. XPS and STM results clearly indicate that ECCO adsorbs selectively on Si(001) via a [2+2] cycloaddition of the strained triple bond without reaction of the ethynyl group. The latter can thus be used for further reactions and multilayer formation, e.g., by means of alkyne-azide coupling. The observed chemoselective reactivity of ECCO on Si(001) is traced back to the direct reaction channel of cyclooctyne [1] in contrast to the precursor-mediated adsorption pathway of the terminal triple bond.

[1] Reutzel et al., J. Phys. Chem. C 120 26284 (2016).