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An approach to helical tubular self-aggregation using C-2-symmetric self-complementary hydrogen-bonding cavity molecules

Stoncius, Sigitas ; Orentas, Edvinas ; Butkus, Eugenius ; Öhrstrom, Lars ; Wendt, Ola LU and Wärnmark, Kenneth LU (2006) In Journal of the American Chemical Society 128(25). p.8272-8285
Abstract
In an approach to helical self-aggregation, C-2-symmetric cavity compounds based on the fusion of the bicyclo[3.3.1] nonane and indole framework and incorporating two 2-pyridone hydrogen-bonding motifs, compounds (-)-4 (pyrrole N-butyl) and (-)-5 (pyrrole N-decyl), have been synthesized. The 2-pyridone AD-DA hydrogen-bonding motif failed to operate in the solid state as demonstrated by X-ray diffraction analysis of (-)-4. Instead, the hydrogen- bonded (D-A) chains center dot center dot center dot O=C-N-H center dot center dot center dot O=C-N-H center dot center dot center dot O=C-N-H center dot center dot center dot, interconnecting columnar stacks, comprise helices of the right-handed (P) chirality motif. In solution, the aggregation of... (More)
In an approach to helical self-aggregation, C-2-symmetric cavity compounds based on the fusion of the bicyclo[3.3.1] nonane and indole framework and incorporating two 2-pyridone hydrogen-bonding motifs, compounds (-)-4 (pyrrole N-butyl) and (-)-5 (pyrrole N-decyl), have been synthesized. The 2-pyridone AD-DA hydrogen-bonding motif failed to operate in the solid state as demonstrated by X-ray diffraction analysis of (-)-4. Instead, the hydrogen- bonded (D-A) chains center dot center dot center dot O=C-N-H center dot center dot center dot O=C-N-H center dot center dot center dot O=C-N-H center dot center dot center dot, interconnecting columnar stacks, comprise helices of the right-handed (P) chirality motif. In solution, the aggregation of (-)-5 was studied by NMR, electronic, and CD spectroscopies, and VPO measurements. These investigations strongly suggest that (-)-5 associates to oligomers in CHCl3 and CH2Cl2 using the 2-pyridone motif, fitting the equal K model, and that pi-stacking can be ruled out as a mode of aggregation. We conclude that the so formed aggregates of (-)-5 have a helical structure, based on the fact that only helical tubular structures can result when enantiomerically pure 5 uses its 2-pyridone AD-DA hydrogenbonding motifs for aggregation. (Less)
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author
; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of the American Chemical Society
volume
128
issue
25
pages
8272 - 8285
publisher
The American Chemical Society (ACS)
external identifiers
  • wos:000238418000044
  • scopus:33745644938
  • pmid:16787092
ISSN
1520-5126
DOI
10.1021/ja061160z
language
English
LU publication?
yes
additional info
The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
id
d69ab4a1-d647-47c8-b3b0-34a0a1caab45 (old id 405961)
date added to LUP
2016-04-01 16:42:14
date last changed
2020-08-19 06:10:57
@article{d69ab4a1-d647-47c8-b3b0-34a0a1caab45,
  abstract     = {In an approach to helical self-aggregation, C-2-symmetric cavity compounds based on the fusion of the bicyclo[3.3.1] nonane and indole framework and incorporating two 2-pyridone hydrogen-bonding motifs, compounds (-)-4 (pyrrole N-butyl) and (-)-5 (pyrrole N-decyl), have been synthesized. The 2-pyridone AD-DA hydrogen-bonding motif failed to operate in the solid state as demonstrated by X-ray diffraction analysis of (-)-4. Instead, the hydrogen- bonded (D-A) chains center dot center dot center dot O=C-N-H center dot center dot center dot O=C-N-H center dot center dot center dot O=C-N-H center dot center dot center dot, interconnecting columnar stacks, comprise helices of the right-handed (P) chirality motif. In solution, the aggregation of (-)-5 was studied by NMR, electronic, and CD spectroscopies, and VPO measurements. These investigations strongly suggest that (-)-5 associates to oligomers in CHCl3 and CH2Cl2 using the 2-pyridone motif, fitting the equal K model, and that pi-stacking can be ruled out as a mode of aggregation. We conclude that the so formed aggregates of (-)-5 have a helical structure, based on the fact that only helical tubular structures can result when enantiomerically pure 5 uses its 2-pyridone AD-DA hydrogenbonding motifs for aggregation.},
  author       = {Stoncius, Sigitas and Orentas, Edvinas and Butkus, Eugenius and Öhrstrom, Lars and Wendt, Ola and Wärnmark, Kenneth},
  issn         = {1520-5126},
  language     = {eng},
  number       = {25},
  pages        = {8272--8285},
  publisher    = {The American Chemical Society (ACS)},
  series       = {Journal of the American Chemical Society},
  title        = {An approach to helical tubular self-aggregation using C-2-symmetric self-complementary hydrogen-bonding cavity molecules},
  url          = {http://dx.doi.org/10.1021/ja061160z},
  doi          = {10.1021/ja061160z},
  volume       = {128},
  year         = {2006},
}