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Issue 2, 2012
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Columnar self-assembly of a 3D-persulfurated coronene asterisk. The dominant role of aryl-sulfur bonds

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Abstract

The synthesis, adsorption behavior, surface structure, and the charge transport properties of a persulfurated coronene asterisk with a 3D-polyaromatic system, namely dodecakis(phenylthio)coronene (DPTC), deposited on HOPG(0001) and Au(111) surfaces, are investigated by means of scanning tunneling microscopy (STM) and spectroscopy (STS). DPTC molecules adsorbed on HOPG(0001) show an orbital mediated tunneling through mainly undisturbed frontier molecular states. DPTC molecules self-assemble on Au(111) into a highly ordered π-stacked columnar “edge-on pattern. The columnar stacking is a gold surface mediated process, as ascertained by fluorescence correlation spectroscopy (FCS). DPTC was monomeric in the precursor solution before assembly. The tunneling spectra of ordered DPTC stacks on Au(111) show an energetic splitting of the frontier molecular states, indicating orbital overlap and supramolecular π–π interactions of adjacent molecules. DPTCs are sufficiently flexible to facilitate dense 1D stacks. The multiple aryl-sulfur bonds play a dominant role in the modulation of the self-assembly properties of the coronenes which in turn affect their electronic properties. Our results encourage further applications in dendrimer chemistry toward molecular electronics, by using the functionalized coronene core and its multidirectional 3D properties.

Graphical abstract: Columnar self-assembly of a 3D-persulfurated coronene asterisk. The dominant role of aryl-sulfur bonds

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Publication details

The article was received on 01 Jun 2011, accepted on 14 Sep 2011 and first published on 17 Nov 2011


Article type: Paper
DOI: 10.1039/C1NJ20472F
Citation: New J. Chem., 2012,36, 477-483
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    Columnar self-assembly of a 3D-persulfurated coronene asterisk. The dominant role of aryl-sulfur bonds

    P. Kowalzik, S. Rathgeber, S. Karthäuser, R. Waser, N. Schnaebele, J. Raimundo and M. Gingras, New J. Chem., 2012, 36, 477
    DOI: 10.1039/C1NJ20472F

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