Journal article
A short designed semi-aromatic organic nanotube – synthesis, chiroptical characterization, and host properties
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.
Language: | English |
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Publisher: | The Royal Society of Chemistry |
Year: | 2014 |
Pages: | 8930-8941 |
ISSN: | 14770539 and 14770520 |
Types: | Journal article |
DOI: | 10.1039/c4ob01683a |
ORCIDs: | Fristrup, Peter |