Synthesis of an Orthogonal Topological Analogue of Helicene.
(2013) In Chemistry: A European Journal 19(44). p.14963-14969- Abstract
- The synthesis of an orthogonal topological pentamer analogue of helicene is presented. This analogue forms a tubular structure with its aromatic systems directed parallel to the axis of propagation, which creates a cavity with the potential to function as a host molecule. The synthetic strategy reported, based on a series of repeating Friedländer condensations that utilize pyrido[3,2-d]pyrimidine moieties as protected amino aldehydes, allows for the facile access of higher generations of helical, tubular structures. As a result of the synthetic strategy, only a helical isomer of the pentamer is possible. The structure and absolute configuration of the pentamer were elucidated from a combination of NMR spectroscopic data, optical... (More)
- The synthesis of an orthogonal topological pentamer analogue of helicene is presented. This analogue forms a tubular structure with its aromatic systems directed parallel to the axis of propagation, which creates a cavity with the potential to function as a host molecule. The synthetic strategy reported, based on a series of repeating Friedländer condensations that utilize pyrido[3,2-d]pyrimidine moieties as protected amino aldehydes, allows for the facile access of higher generations of helical, tubular structures. As a result of the synthetic strategy, only a helical isomer of the pentamer is possible. The structure and absolute configuration of the pentamer were elucidated from a combination of NMR spectroscopic data, optical properties, X-ray structures, and by comparison of an experimental electronic circular dichroism spectrum to a calculated spectrum. (Less)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/4143520
- author
- Wixe, Torbjörn LU ; Wallentin, Carl-Johan LU ; Johnson, Magnus LU ; Fristrup, Peter ; Lidin, Sven LU and Wärnmark, Kenneth LU
- organization
- publishing date
- 2013
- type
- Contribution to journal
- publication status
- published
- subject
- in
- Chemistry: A European Journal
- volume
- 19
- issue
- 44
- pages
- 14963 - 14969
- publisher
- Wiley-Blackwell
- external identifiers
-
- pmid:24105657
- wos:000331300600027
- scopus:84885855292
- pmid:24105657
- ISSN
- 1521-3765
- DOI
- 10.1002/chem.201302278
- language
- English
- LU publication?
- yes
- id
- b311e627-6908-47ae-82dc-911c07b83da1 (old id 4143520)
- date added to LUP
- 2016-04-01 10:14:28
- date last changed
- 2025-10-14 10:16:04
@article{b311e627-6908-47ae-82dc-911c07b83da1,
abstract = {{The synthesis of an orthogonal topological pentamer analogue of helicene is presented. This analogue forms a tubular structure with its aromatic systems directed parallel to the axis of propagation, which creates a cavity with the potential to function as a host molecule. The synthetic strategy reported, based on a series of repeating Friedländer condensations that utilize pyrido[3,2-d]pyrimidine moieties as protected amino aldehydes, allows for the facile access of higher generations of helical, tubular structures. As a result of the synthetic strategy, only a helical isomer of the pentamer is possible. The structure and absolute configuration of the pentamer were elucidated from a combination of NMR spectroscopic data, optical properties, X-ray structures, and by comparison of an experimental electronic circular dichroism spectrum to a calculated spectrum.}},
author = {{Wixe, Torbjörn and Wallentin, Carl-Johan and Johnson, Magnus and Fristrup, Peter and Lidin, Sven and Wärnmark, Kenneth}},
issn = {{1521-3765}},
language = {{eng}},
number = {{44}},
pages = {{14963--14969}},
publisher = {{Wiley-Blackwell}},
series = {{Chemistry: A European Journal}},
title = {{Synthesis of an Orthogonal Topological Analogue of Helicene.}},
url = {{http://dx.doi.org/10.1002/chem.201302278}},
doi = {{10.1002/chem.201302278}},
volume = {{19}},
year = {{2013}},
}