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Synthesis of N-substituted Pyrido[4,3-d]pyrimidines for the Large-Scale Production of Self-Assembled Rosettes and Nanotubes
Date
2013-11-15
Author
DURMUS, Asuman
Günbaş, Emrullah Görkem
Farmer, Steven C.
Ohnstead, Marilyn M.
MASCAL, Mark
Legese, Belete
Cho, Jae-Young
Beingessner, Rachel L.
Yamazaki, Takeshi
Fenniri, Hicham
Metadata
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This work is licensed under a
Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License
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N-substituted pyrido[4,3-d]pyrimidines are heterocycles which exhibit the asymmetric hydrogen bonding codes of both guanine and cytosine at 60 degrees angles to each other, such that the molecules self-organize unambiguously into a cyclic hexamer, assembled via 18 intermolecular hydrogen bonds. The synthesis is straightforward and can be concluded in six steps from the commercially available malononitrile dimer. X-ray crystallographic analysis of the supermacrocyclic structure shows an undulating disk with a ca. 10.5 angstrom cavity, the centers of which do not overlap sufficiently to describe a channel in the solid state. However, AFM, SEM, and TEM imaging in solution reveals the formation of 1D nanostructures in agreement with their self-assembly into rosette supermacrocycles, which then stack linearly to form rosette nanotubes.
Subject Keywords
DNA-BASE HYBRID
,
C BASE
,
MOLECULES
URI
https://hdl.handle.net/11511/40430
Journal
JOURNAL OF ORGANIC CHEMISTRY
DOI
https://doi.org/10.1021/jo4019792
Collections
Department of Chemistry, Article