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Oxidation of an Organic Adlayer: A Bird’s Eye View

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Institute of Surface Chemistry and Catalysis and Institute of Theoretical Chemistry, Ulm University, D-89069 Ulm, Germany
Cite this: J. Am. Chem. Soc. 2012, 134, 21, 8817–8822
Publication Date (Web):May 9, 2012
https://doi.org/10.1021/ja302593v
Copyright © 2012 American Chemical Society

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    Abstract

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    The reaction of O2 with an adlayer of the oligopyridine 2-phenyl-4,6-bis(6-(pyridine-2-yl)-4-(pyridine-4-yl)-pyridine-2-yl)pyrimidine (2,4′-BTP), adsorbed on the (111) surfaces of silver and gold and on HOPG – which can be considered as a model system for inorganic|organic contacts – was investigated by fast scanning tunneling microscopy (video STM) and dispersion corrected density functional theory (DFT-D) calculations. Only on Ag(111), oxidation of the 2,4′-BTP adlayer was observed, which is related to the fact that under the experimental conditions O2 adsorbs dissociatively on this surface leading to reactive O adatoms, but not on Au(111) or HOPG . There is a distinct regiospecifity of the oxidation reaction caused by intermolecular interactions. In addition, the oxidation leads to a chiral ordering. The relevance of these findings for reactions involving organic monolayers is discussed.

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    Experimental and theoretical details, additional STM images and MC based calculations. This material is available free of charge via the Internet at http://pubs.acs.org.

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