Regensburg 2019 – wissenschaftliches Programm
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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).