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Dehydrogenation of the Liquid Organic Hydrogen Carrier System 2-methylindole/2-methylindoline/2-methyloctahydroindole on Pt(111)

Dehydrogenation of the Liquid Organic Hydrogen Carrier System 2-methylindole/2-methylindoline/2-methyloctahydroindole on Pt(111)

Philipp Bachmann, Johann Steinhauer, Florian Späth, Fabian Düll, Udo Bauer, Roman Eschenbacher, Felix Hemauer, Marlene Scheuermeyer, Andreas Bösmann, Miriam Büttner, Christian Neiß, Andreas Görling, Peter Wasserscheid, etc.

J Chem Phys. 2019 Oct 14;151(14):144711.

PMID: 31615244

Abstract:

Among other N-heterocycles, indole and its substituted derivatives, such as methylindoles, are considered promising Liquid Organic Hydrogen Carriers (LOHCs) for the storage of renewable energy. We used X-ray photoelectron spectroscopy (XPS), temperature programmed desorption (TPD), and density-functional theory (DFT) to investigate the low temperature adsorption and consecutive dehydrogenation reaction during heating of 2-methylindole, 2-methylindoline, and 2-methyloctahydroindole on Pt(111) and their viability as the LOHC system. In the photoemission experiments, for all Hx-2-methylindoles, we find deprotonation at the NH bond starting between 240 and 300 K, resulting in a 2-methylindolide species. Simultaneously or before this reaction step, the dehydrogenation of 2-methyloctahydroindole via 2-methylindoline and 2-methylindole intermediates is observed. For 2-methyloctahydroindole, we also find π-allyl intermediates above 230 K. Starting at ∼390 K, decomposition of the remaining 2-methylindolide species takes place under the conditions of our surface science experiments. DFT calculations give insight into the relative energies of the various species, reaction intermediates, and their isomers both in the gas phase and on the Pt(111) surface.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP95205	2-Methylindole		95-20-5	Price

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