Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 19, Issue 14, Pages 4480-4495Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201203444
Keywords
aggregation; aromatic compounds; macrocycles; nanostructures; template synthesis
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Funding
- Deutsche Forschungsgemeinschaft (DFG)
- Sonderforschungsbereich (SFB) [624]
- Fonds der Chemischen Industrie (FCI)
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We present the efficient synthesis of a new molecular spoked-wheel structure (MSW-3). Two derivatives with diameters of approximately 4nm 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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