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Synthesis of an Orthogonal Topological Analogue of Helicene
Author(s) -
Wixe Torbjörn,
Wallentin CarlJohan,
Johnson Magnus T.,
Fristrup Peter,
Lidin Sven,
Wärnmark Kenneth
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201302278
Subject(s) - helicene , pentamer , circular dichroism , chemistry , molecule , topology (electrical circuits) , stereochemistry , crystallography , mathematics , organic chemistry , combinatorics , biochemistry
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.