Synthesis of an Orthogonal Topological Analogue of Helicene.

Torbjörn Wixe, Carl-Johan Wallentin, Magnus Johnson, Peter Fristrup, Sven Lidin, Kenneth Wärnmark

Research output: Contribution to journalArticlepeer-review


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.
Original languageEnglish
Pages (from-to)14963-14969
JournalChemistry: A European Journal
Issue number44
Publication statusPublished - 2013

Subject classification (UKÄ)

  • Chemical Sciences


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