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Helical Molecular Programming: Folding of Oligopyridine‐dicarboxamides into Molecular Single Helices
- Source :
- Chemistry - A European Journal; July 2001, Vol. 7 Issue: 13 p2798-2809, 12p
- Publication Year :
- 2001
-
Abstract
- Molecular strands composed of alternating 2,6‐diaminopyridine and 2,6‐pyridinedicarbonyl units have been designed to self‐organize into single stranded helical structures upon forming intramolecular hydrogen bonds. Pentameric strands 11, 12, and 14, heptameric strands 1and 20, and undecameric strand 15have been synthesized using stepwise convergent strategies. Single helical conformations have been characterized in the solid state by single crystal X‐ray diffraction analysis for four of these compounds. Helices from pentameric strands 12and 14extend over one turn, and helices from heptameric 20and undecameric 15species extend to one and a half and two and a half turns, respectively. Intramolecular hydrogen bonds are responsible for the strong bending of the strands. 1H NMR shifts both in polar and nonpolar organic solvents indicate intramolecular overlap between the peripheral aromatic groups. Thus, helical conformations also predominate in solution. Molecular stochastic dynamic simulations of strand folding starting from a high energy extended linear conformer show a rapid (600 ps at 300 K) conversion into a stable helical conformation.
Details
- Language :
- English
- ISSN :
- 09476539 and 15213765
- Volume :
- 7
- Issue :
- 13
- Database :
- Supplemental Index
- Journal :
- Chemistry - A European Journal
- Publication Type :
- Periodical
- Accession number :
- ejs2253319
- Full Text :
- https://doi.org/10.1002/1521-3765(20010702)7:13<2798::AID-CHEM2798>3.0.CO;2-L