Molecular Spoked Wheels: Synthesis and Self-Assembly Studies on Rigid Nanoscale 2D Objects

Authors

  • A. Vikas Aggarwal,

    1. Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn (Germany), Fax: (+49) 228-73-5662
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  • Dr. Stefan-S. Jester,

    1. Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn (Germany), Fax: (+49) 228-73-5662
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  • Sara Mehdizadeh Taheri,

    1. Physikalische Chemie I, Universität Bayreuth, Universitätsstrasse 30, 95440 Bayreuth (Germany)
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  • Prof. Dr. Stephan Förster,

    Corresponding author
    1. Physikalische Chemie I, Universität Bayreuth, Universitätsstrasse 30, 95440 Bayreuth (Germany)
    • Physikalische Chemie I, Universität Bayreuth, Universitätsstrasse 30, 95440 Bayreuth (Germany)
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  • Prof. Dr. Sigurd Höger

    Corresponding author
    1. Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn (Germany), Fax: (+49) 228-73-5662
    • Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn (Germany), Fax: (+49) 228-73-5662
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Abstract

We present the efficient synthesis of a new molecular spoked-wheel structure (MSW-3). Two derivatives with diameters of approximately 4 nm have been prepared. By highlighting the importance of pseudo-high-dilution conditions during cyclization, we were able to access the compounds on a several hundred milligram scale. In addition to the standard characterization (NMR spectroscopy, MS), we describe a detailed investigation of the optical properties of the fluorescent MSWs by comparison with appropriate model chromophores. Furthermore, a comprehensive study of the structure in solution by means of light- and X-ray scattering experiments has been conducted. Scanning tunneling microscopy (STM) revealed the two-dimensional organization of the molecules on highly oriented pyrolytic graphite and emphasized the spoked-wheel structure. The diameter of these molecules measured by small-angle X-ray scattering is in very good agreement with that obtained from STM and matches the results of molecular modeling. This confirms the rigidifying effect of the spokes, which results in highly shape-persistent nanometer-sized oblate organic compounds.

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