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Issue 10, 2019
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The fate of bromine after temperature-induced dehydrogenation of on-surface synthesized bisheptahelicene

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Abstract

The on-surface synthesis of bisheptahelicene by Ullmann coupling of 9-bromoheptahelicene on Au(111) and its temperature-induced dehydrogenation is studied using temperature-programmed reaction spectroscopy and time-of-flight secondary ion mass spectrometry. Specific dehydrogenation products of bisheptahelicene after loss of 6, 8 and 10 hydrogen atoms are identified, corresponding to molecules having undergone Diels–Alder transformations and intramolecular C–C coupling reactions. By combining with atomic hydrogen produced by dehydrogenation, the Ullmann coupling side-product bromine desorbs as HBr. H2 desorption emerges only after all Br has desorbed. Such characteristic behavior is explained by a kinetic model which explicitly considers the coverage of transient atomic H on the surface. Heating experiments performed with saturated layers of different Br-containing molecules reveal that the onset of HBr desorption depends strictly on the dehydrogenation step and therefore on the structure of the molecules.

Graphical abstract: The fate of bromine after temperature-induced dehydrogenation of on-surface synthesized bisheptahelicene

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Publication details

The article was received on 23 Oct 2018, accepted on 15 Jan 2019 and first published on 15 Jan 2019


Article type: Edge Article
DOI: 10.1039/C8SC04720K
Chem. Sci., 2019,10, 2998-3004
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    The fate of bromine after temperature-induced dehydrogenation of on-surface synthesized bisheptahelicene

    A. Mairena, M. Baljozovic, M. Kawecki, K. Grenader, M. Wienke, K. Martin, L. Bernard, N. Avarvari, A. Terfort, K. Ernst and C. Wäckerlin, Chem. Sci., 2019, 10, 2998
    DOI: 10.1039/C8SC04720K

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