Synthesis of an Orthogonal Topological Analogue of Helicene.

Summary, in English

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 pyrido[3,2-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.

• Author: Torbjörn Wixe; Carl-Johan Wallentin; Magnus Johnson; Peter Fristrup; Sven Lidin; Kenneth Wärnmark
• Department/s: Centre for Analysis and Synthesis; Department of Chemistry
• Publishing year: 2013
• Language: English
• Pages: 14963-14969
• Publication/Series: Chemistry: A European Journal
• Volume: 19
• Issue: 44
• Links: http://dx.doi.org/10.1002/chem.201302278
• Document type: Journal article
• Publisher: Wiley-Blackwell
• Topic: Chemical Sciences
• Status: Published
• ISBN/ISSN/Other: ISSN: 1521-3765