Fast Oxidative Cyclooligomerization towards Low‐ and High‐Symmetry Thiophene Macrocycles |
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| Authors: | Dr. Stefan K. Maier Georgiy Poluektov Dr. Stefan‐S. Jester Prof. Dr. Heiko M. Möller Prof. Dr. Sigurd Höger |
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| Affiliation: | 1. Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universit?t Bonn, Bonn, Germany), Fax;2. +49)?331‐977‐5092;3. Institut für Chemie, Universit?t Potsdam, Golm, Germany), Fax;4. +49)?228‐73‐5662 |
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| Abstract: | Macrocycles with quaterthiophene subunits were obtained by cyclooligomerization by direct oxidative coupling of unsubstituted dithiophene moieties. The rings were closed with high selectivity by an α,β′‐connection of the thiophenes as proven by NMR spectroscopy. The reaction of the precursor with terthiophene moieties yielded the symmetric α,α′‐linked macrocycle in low yield together with various differently connected isomers. Blocking of the β‐position of the half‐rings yielded selectively the α,α′‐linked macrocycle. Selected cyclothiophenes were investigated by scanning tunneling microscopy, which displayed the formation of highly ordered 2D crystalline monolayers. |
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| Keywords: | cyclooligomers scanning tunneling microscopy self-assembled monolayers shape-persistent macrocycles thiophenes |
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