A short designed semi-aromatic organic nanotube – synthesis, chiroptical characterization, and host properties

Torbjörn Wixe, Niels Johan Christensen, Sven Lidin, Peter Fristrup, Kenneth Wärnmark

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

The first generation of an organic nanotube based on the enantiomerically pure bicyclo[3.3.1]nonane framework is presented. The helical tube synthesised is the longest to date having its aromatic systems oriented parallel to the axis of propagation (length 26 Å and inner diameter 11 Å according to molecular dynamics simulations in chloroform). The synthesis of the tube, a heptamer, is based on a series of Friedländer condensations and the use of pyrido[3,2-d]pyrimidine units as masked 2-amino aldehydes, as a general means to propagate organic tubular structures and the introduction of a methoxy group for modification toward solubility and functionalization are described. The electronic CD spectra of the tube and molecular intermediates are correlated with theoretical spectra calculated with time-dependent density functional theory to characterize the chirality of the tube. Both experimental (NMR-titrations) and theoretical (molecular dynamics simulations) techniques are used to investigate the use of the tube as a receptor for the acetylcholine and guanidinium cations, respectively.
Original languageEnglish
JournalOrganic & Biomolecular Chemistry
Volume12
Issue number44
Pages (from-to)8930-8941
ISSN1477-0520
DOIs
Publication statusPublished - 2014

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