SKM 2023 – wissenschaftliches Programm
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O: Fachverband Oberflächenphysik
O 48: Focus Session: Semiconductor Surface Chemistry – from Reaction Mechanisms to Well-Ordered Interfaces I
O 48.4: Vortrag
Mittwoch, 29. März 2023, 11:45–12:00, GER 38
Organic molecular architectures synthesized by means of solution-based click chemistry on functionalized silicon surfaces — •Timo Glaser1, Jannick Alexander Peters1, Christian Länger1, Dominik Scharf2, Jannick Meinecke2, Ulrich Koert2, and Michael Dürr1 — 1Institut für Angewandte Physik und Zentrum für Materialforschung, Justus-Liebig-Universität Giessen, Germany — 2Fachbereich Chemie, Philipps-Universität Marburg, Germany
The application of organic click chemistry to selectively functionalized silicon surfaces may open the route to synthesizing new organic molecular architectures on silicon. However, this scheme seems to be an experimental contradiction since click reactions are performed in the presence of a catalyst dissolved in a solvent whereas the highly reactive Si(001) surface is prepared and stored under UHV conditions. Here we show how to combine surface functionalization performed under UHV conditions with solution-based alkyne-azide click reactions. The UHV-based functionalization of Si(001) was realized via chemoselective adsorption of ethinyl cyclopropyl cyclooctyne (ECCO) from the gas phase. The samples were then directly transferred from UHV into the reaction solution where alternating layers of bisazide and bisalkine were coupled subsequently step by step without exposure to ambient conditions. Each reaction step was monitored by means of XPS in UHV and the selectivity of the reaction schemes in use was demonstrated. Using optimized copper(I) catalysts, reaction yields of up to 75 % were obtained.