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DOI: 10.1055/s-0028-1087311
An H-Bond Tetrameric Rosette
Contributor(s):Timothy M. Swager, Fei WangUniversity of British Columbia, Vancouver, Canada
G^C Quartet - A DNA-Inspired Janus-GC Heterocycle: Synthesis, Structural Analysis, and Self-Organization
J. Am. Chem. Soc. 2008, 130: 12860-12861
Publication History
Publication Date:
20 November 2008 (online)
Key words
H-bond - self-assembly - tetrameric rosette
Significance
Reported was the synthesis and assembly of a self-complementary guanine-cytosine heterocyclic molecule. The central pyrrol ring keeps the DDA-AAD faces at precisely 90º, thus facilitating the self-assembly of such molecules into a tetrameric rosette. The structure of the H-bond tertramer was verified by ESI-MS, variable temperature ¹H NMR spectroscopy and DOSY.
Comment
H-bond-assisted self-assembly is an important method to build useful and interesting molecular structures. In this example, the tetramer forms via H-bonding without dependence on extra metal ion or peripheral components. It will be interesting to further study the molecule in higher-ordered systems, such as 3D assembly or liquid crystalline behaviors.