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Synthesis of an Orthogonal Topological Analogue of Helicene.

Författare

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.

Publiceringsår

2013

Språk

Engelska

Sidor

14963-14969

Publikation/Tidskrift/Serie

Chemistry: A European Journal

Volym

19

Issue

44

Dokumenttyp

Artikel i tidskrift

Förlag

Wiley-Blackwell

Ämne

  • Chemical Sciences

Status

Published

ISBN/ISSN/Övrigt

  • ISSN: 1521-3765