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3123622 
Journal Article 
Synthesis of Pyrene-Fused Pyrazaacenes on Metal Surfaces: Toward One-Dimensional Conjugated Nanostructures 
Jiang, Li; Papageorgiou, AC; Oh, SC; Saglam, O; Reichert, J; Duncan, DA; Zhang, Y; Klappenberger, F; Guo, Y; Allegretti, F; More, S; Bhosale, R; Mateo-Alonso, A; Barth, JV 
2016 
1 
ACS Nano
ISSN: 1936-0851
EISSN: 1936-086X 
AMER CHEMICAL SOC 
WASHINGTON 
10 
1 
1033-1041 
English 
26651905 
WOS:000369115800112 
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. 
imine; Schiff base; cyclocondensation; STM; XPS; ultrahigh vacuum