A short designed semi-aromatic organic nanotube - synthesis, chiroptical characterization, and host properties.
(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)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/4738607
- author
- Wixe, Torbjörn LU ; Christensen, Niels Johan ; Lidin, Sven LU ; Fristrup, Peter and Wärnmark, Kenneth LU
- organization
- publishing date
- 2014
- 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
- pmid:25271821
- 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
- 2016-04-01 11:13:03
- date last changed
- 2023-08-31 20:57:44
@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}},
doi = {{10.1039/c4ob01683a}},
volume = {{12}},
year = {{2014}},
}