Synthesis of an Orthogonal Topological Analogue of Helicene

Torbjörn Wixe, Carl‐Johan Wallentin, Magnus T. Johnson, Peter Fristrup, Sven Lidin, Kenneth Wärnmark

Research output: Contribution to journalJournal articleResearchpeer-review

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 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
JournalChemistry: A European Journal
Volume19
Issue number44
Pages (from-to)14963-14969
ISSN0947-6539
DOIs
Publication statusPublished - 2013

Keywords

  • Bicyclic compounds
  • Circular dichroism
  • Helical structures
  • Pyridopyridines
  • Quinolines

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