An approach to helical tubular self-aggregation using C-2-symmetric self-complementary hydrogen-bonding cavity molecules
(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)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/405961
- author
- Stoncius, Sigitas ; Orentas, Edvinas ; Butkus, Eugenius ; Öhrstrom, Lars ; Wendt, Ola LU and Wärnmark, Kenneth LU
- organization
- publishing date
- 2006
- 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
- 2022-01-28 21:33:59
@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}}, }