Journal
ACS NANO
Volume 10, Issue 1, Pages 1033-1041Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsnano.5b06340
Keywords
imine; Schiff base; cyclocondensation; STM; XPS; ultrahigh vacuum
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Funding
- ERC Advanced Grant MolArt [247299]
- Excellence Clusters Munich-Centre for Advanced Photonics (MAP)
- Nanosystems Initiative Munich (NIM) - German Research Foundation (DFG) via the German Excellence Initiative
- China Scholarship Council (CSC)
- Marie Curie International Incoming Fellowship (Project NANOULOP)
- Humboldt foundation
- Helmholz-Zentrum Berlin
- Freiburg Institute for Advanced Studies (FRIAS)
- Basque Science Foundation for Science (Ikerbasque), POLYMAT
- University of the Basque Country (SGIker)
- Deutsche Forschungsgemeinschaft [AU 373/3-1, MA 5215/4-1]
- Gobierno de Espana (Ministerio de Economia y Competitividad) [MAT2012-35826]
- Gobierno Vasco (BERC program) [PC2015-1-01(06-37)]
- Diputacion Foral de Guipuzcoa [2015-CIEN-000054-01]
- European Union [618247]
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We investigated the synthesis of one-dimensional nanostructures via Schiff base (imine) formation on three close-packed coinage metal (Au, Ag, and Cu) surfaces under ultrahigh vacuum conditions. We demonstrate the feasibility of forming pyrene-fused pyrazaacene-based oligomers on the Ag(111) surface by thermal annealing of tetraketone and tetraamine molecules, which were designed to afford cyclocondensation products. Direct visualization by scanning tunneling microscopy of reactants, intermediates, and products with submolecular resolution and the analysis' of their statistical distribution in dependence of stoichiometry and annealing temperature together with the inspection of complementary X-ray photoelectron spectroscopy signatures provide unique insight in the reaction mechanism, its limitations, and the role of the supporting substrate. In contrast to the reaction on Ag(111), the reactants desorb from the Au(111) surface before reacting, whereas they decompose on the Cu(111) Surface during the relevant thermal treatment.
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