Chemoselective Reactivity of Bifunctional Cyclooctynes on Si(001)
| Autor: | Christian Länger, Ulrich Höfer, M.A. Lipponer, Ulrich Koert, Niels Münster, Marcel Reutzel, Michael Dürr |
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| Rok vydání: | 2016 |
| Předmět: |
Silicon
FOS: Physical sciences chemistry.chemical_element 02 engineering and technology 010402 general chemistry 01 natural sciences chemistry.chemical_compound Physics - Chemical Physics Organic chemistry Reactivity (chemistry) Physical and Theoretical Chemistry Bifunctional Chemical Physics (physics.chem-ph) Condensed Matter - Materials Science Chemistry Reaction step Dangling bond Materials Science (cond-mat.mtrl-sci) 021001 nanoscience & nanotechnology Triple bond Combinatorial chemistry 0104 chemical sciences Surfaces Coatings and Films Electronic Optical and Magnetic Materials General Energy Surface modification 0210 nano-technology Selectivity |
| Zdroj: | The Journal of Physical Chemistry C. 120:26284-26289 |
| ISSN: | 1932-7455 1932-7447 |
| Popis: | Controlled organic functionalization of silicon surfaces as integral part of semiconductor technology offers new perspectives for a wide range of applications. The high reactivity of the silicon dangling bonds, however, presents a major hindrance for the first basic reaction step of such a functionalization, i.e., the chemoselective attachment of bifunctional organic molecules on the pristine silicon surface. We overcome this problem by employing cyclooctyne as the major building block of our strategy. Functionalized cyclooctynes are shown to react on Si(001) selectively via the strained cyclooctyne triple bond while leaving the side groups intact. The achieved selectivity originates from the distinctly different adsorption dynamics of the separate functionalities: A direct adsorption pathway is demonstrated for cyclooctyne as opposed to the vast majority of other organic functional groups. The latter ones react on Si(001) via a metastable intermediate which makes them effectively unreactive in competition with the direct pathway of cyclooctyne's strained triple bond. 16 pages, 5 figures, TOC figure |
| Databáze: | OpenAIRE |
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