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

Wixe, Torbjörn LU ; Christensen, Niels Johan; Lidin, Sven LU ; Fristrup, Peter and Wärnmark, Kenneth LU (2014) In Organic and Biomolecular Chemistry 12(44). p.8930-8941
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... (More)
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. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Organic and Biomolecular Chemistry
volume
12
issue
44
pages
8930 - 8941
publisher
Royal Society of Chemistry
external identifiers
  • pmid:25271821
  • wos:000344236200017
  • scopus:84908374313
ISSN
1477-0539
DOI
10.1039/c4ob01683a
language
English
LU publication?
yes
id
1a8446a8-b6a4-426b-84f0-1738fee3d908 (old id 4738607)
date added to LUP
2014-11-17 11:32:08
date last changed
2017-01-01 04:15:49
@article{1a8446a8-b6a4-426b-84f0-1738fee3d908,
  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.},
  author       = {Wixe, Torbjörn and Christensen, Niels Johan and Lidin, Sven and Fristrup, Peter and Wärnmark, Kenneth},
  issn         = {1477-0539},
  language     = {eng},
  number       = {44},
  pages        = {8930--8941},
  publisher    = {Royal Society of Chemistry},
  series       = {Organic and Biomolecular Chemistry},
  title        = {A short designed semi-aromatic organic nanotube - synthesis, chiroptical characterization, and host properties.},
  url          = {http://dx.doi.org/10.1039/c4ob01683a},
  volume       = {12},
  year         = {2014},
}