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

Summary, in English

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.

• Author: Torbjörn Wixe; Niels Johan Christensen; Sven Lidin; Peter Fristrup; Kenneth Wärnmark
• Department/s: Centre for Analysis and Synthesis; NanoLund: Centre for Nanoscience
• Publishing year: 2014
• Language: English
• Pages: 8930-8941
• Publication/Series: Organic and Biomolecular Chemistry
• Volume: 12
• Issue: 44
• Links: http://dx.doi.org/10.1039/c4ob01683a
• Document type: Journal article
• Publisher: Royal Society of Chemistry
• Topic: Chemical Sciences
• Status: Published
• ISBN/ISSN/Other: ISSN: 1477-0539