NDLI: Comparing Ullmann Coupling on Noble Metal Surfaces: On-Surface Polymerization of 1,3,6,8-Tetrabromopyrene on Cu(111) and Au(111)

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Comparing Ullmann Coupling on Noble Metal Surfaces: On-Surface Polymerization of 1,3,6,8-Tetrabromopyrene on Cu(111) and Au(111)

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Stöhr, Meike Nguyen, Manh-thuong Studener, Florian Pham, Tuan Anh Song, Fei Li, Zheshen
Description	Author Affiliation: Pham TA ( Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands. t.a.pham@rug.nl.); Song F ( Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.); Nguyen MT ( The Abdus Salam International Centre for Theoretical Physics, Strada Costiera, 11, 34151, Trieste, Italy.); Li Z ( ISA, Department of Physics and Astronomy, University of Aarhus, 8000, Aarhus C, Denmark.); Studener F ( Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.); Stöhr M ( Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands. m.a.stohr@rug.nl.)
Abstract	The on-surface polymerization of 1,3,6,8-tetrabromopyrene $(Br_{4}Py)$ on Cu(111) and Au(111) surfaces under ultrahigh vacuum conditions was investigated by a combination of scanning tunneling microscopy (STM), X-ray photoelectron spectroscopy (XPS) and density functional theory (DFT) calculations. Deposition of $Br_{4}Py$ on Cu(111) held at 300 K resulted in a spontaneous debromination reaction, generating the formation of a branched coordination polymer network stabilized by C−Cu−C bonds. After annealing at 473 K, the C−Cu−C bonds were converted to covalent C−C bonds, leading to the formation of a covalently linked molecular network of short oligomers. In contrast, highly ordered self-assembled two-dimensional (2D) patterns stabilized by both Br−Br halogen and Br−H hydrogen bonds were observed upon deposition of $Br_{4}Py$ on Au(111) held at 300 K. Subsequent annealing of the sample at 473 K led to a dissociation of the C−Br bonds and the formation of disordered metal-coordinated molecular networks. Further annealing at 573 K resulted in the formation of covalently linked disordered networks. Importantly, we found that the chosen substrate not only plays an important role as catalyst for the Ullmann reaction, but also influences the formation of different types of intermolecular bonds and thus, determines the final polymer network morphology. DFT calculations further support our experimental findings obtained by STM and XPS and add complementary information on the reaction pathway of $Br_{4}Py$ on the different substrates.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	17
Volume Number	22
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2016-04-18
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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