Synthesis of an Orthogonal Topological Analogue of Helicene |
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Authors: | Torbjörn Wixe Dr Carl‐Johan Wallentin Dr Magnus T Johnson Dr Peter Fristrup Prof Sven Lidin Prof Kenneth Wärnmark |
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Institution: | 1. Centre for Analysis and Synthesis, Lund University, P.O. Box 124, 221 00, Lund (Sweden), Fax: (+46)?46‐2228209;2. Department of Chemistry, Building 201, Technical University of Denmark, 2800 Kgs. Lyngby (Denmark) |
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Abstract: | The synthesis of an orthogonal topological pentamer analogue of helicene is presented. This analogue forms a tubular structure with its aromatic systems directed parallel to the axis of propagation, which creates a cavity with the potential to function as a host molecule. The synthetic strategy reported, based on a series of repeating Friedländer condensations that utilize pyrido3,2‐d]pyrimidine moieties as protected amino aldehydes, allows for the facile access of higher generations of helical, tubular structures. As a result of the synthetic strategy, only a helical isomer of the pentamer is possible. The structure and absolute configuration of the pentamer were elucidated from a combination of NMR spectroscopic data, optical properties, X‐ray structures, and by comparison of an experimental electronic circular dichroism spectrum to a calculated spectrum. |
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Keywords: | bicyclic compounds circular dichroism helical structures pyridopyridines quinolines |
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