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Design and synthesis of a C-2-symmetric self-complementary hydrogen-bonding cleft molecule based on the bicyclo[3.3.1]nonane and 4-oxo-5-azaindole framework. Formation of channels and inclusion complexes in the solid state

Stoncius, S; Butkus, E; Zilinskas, A; Larsson, K; Ohrstrom, L; Berg, Ulf LU and Wärnmark, Kenneth LU (2004) In Journal of Organic Chemistry 69(16). p.5196-5203
Abstract
The synthesis of a C-2-symmetric cleft molecule 2 based on the fused framework between bicyclo-[3.3. 1] nonane and 4-oxo-5-azaindole, incorporating a self-complementary hydrogen-bonding motif, in both racemic and enantiomerically pure forms is reported. This cleft molecule is reminiscent of analogues of Troger's base though with different cleft dimensions and tilt angles. The framework of 2 provides a building block for the construction of self-assembled hydrogen-bonded supramolecular structures. The solid-state structure of 2 is highly influenced by the limited solubility of (+/-)-2 and (-)-2. The solvents interact with the potential hydrogen-bonding motifs of (+/-)-2 and (-)-2, forming different three-dimensional structures as revealed... (More)
The synthesis of a C-2-symmetric cleft molecule 2 based on the fused framework between bicyclo-[3.3. 1] nonane and 4-oxo-5-azaindole, incorporating a self-complementary hydrogen-bonding motif, in both racemic and enantiomerically pure forms is reported. This cleft molecule is reminiscent of analogues of Troger's base though with different cleft dimensions and tilt angles. The framework of 2 provides a building block for the construction of self-assembled hydrogen-bonded supramolecular structures. The solid-state structure of 2 is highly influenced by the limited solubility of (+/-)-2 and (-)-2. The solvents interact with the potential hydrogen-bonding motifs of (+/-)-2 and (-)-2, forming different three-dimensional structures as revealed by X-ray diffraction analysis. In the solid state (+/-)-(2)(2)(.)5DMF forms hydrogen-bonded pleated band structures that build up three-dimensional pens between adjacent bands in which two molecules of DMF are trapped. In contrast, the aggregate obtained from (-)-2, (-)-2(.)2AcOH, showed infinite bands of complex constitution. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Organic Chemistry
volume
69
issue
16
pages
5196 - 5203
publisher
The American Chemical Society
external identifiers
  • wos:000223008100005
  • pmid:15287761
  • scopus:3543032191
ISSN
1520-6904
DOI
10.1021/jo035869p
language
English
LU publication?
yes
id
6390e82f-0d45-4dae-b5a1-6c8ce3ee8ff2 (old id 139438)
date added to LUP
2007-07-10 14:38:42
date last changed
2017-09-10 03:48:35
@article{6390e82f-0d45-4dae-b5a1-6c8ce3ee8ff2,
  abstract     = {The synthesis of a C-2-symmetric cleft molecule 2 based on the fused framework between bicyclo-[3.3. 1] nonane and 4-oxo-5-azaindole, incorporating a self-complementary hydrogen-bonding motif, in both racemic and enantiomerically pure forms is reported. This cleft molecule is reminiscent of analogues of Troger's base though with different cleft dimensions and tilt angles. The framework of 2 provides a building block for the construction of self-assembled hydrogen-bonded supramolecular structures. The solid-state structure of 2 is highly influenced by the limited solubility of (+/-)-2 and (-)-2. The solvents interact with the potential hydrogen-bonding motifs of (+/-)-2 and (-)-2, forming different three-dimensional structures as revealed by X-ray diffraction analysis. In the solid state (+/-)-(2)(2)(.)5DMF forms hydrogen-bonded pleated band structures that build up three-dimensional pens between adjacent bands in which two molecules of DMF are trapped. In contrast, the aggregate obtained from (-)-2, (-)-2(.)2AcOH, showed infinite bands of complex constitution.},
  author       = {Stoncius, S and Butkus, E and Zilinskas, A and Larsson, K and Ohrstrom, L and Berg, Ulf and Wärnmark, Kenneth},
  issn         = {1520-6904},
  language     = {eng},
  number       = {16},
  pages        = {5196--5203},
  publisher    = {The American Chemical Society},
  series       = {Journal of Organic Chemistry},
  title        = {Design and synthesis of a C-2-symmetric self-complementary hydrogen-bonding cleft molecule based on the bicyclo[3.3.1]nonane and 4-oxo-5-azaindole framework. Formation of channels and inclusion complexes in the solid state},
  url          = {http://dx.doi.org/10.1021/jo035869p},
  volume       = {69},
  year         = {2004},
}