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Synthesis of N‑substituted Pyrido[4,3‑d]pyrimidines for the Large-Scale Production of Self-Assembled Rosettes and Nanotubes

N-substituted pyrido[4,3-d]pyrimidines are heterocycles which exhibit the asymmetric hydrogen bonding codes of both guanine and cytosine at 60° angles to each other, such that the molecules self-organize unambiguously into a cyclic hexamer, assembled via 18 intermolecular hydrogen bonds. The synthes...

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Bibliographic Details
Published in:Journal of organic chemistry 2013-11, Vol.78 (22), p.11421-11426
Main Authors: Durmus, Asuman, Gunbas, Gorkem, Farmer, Steven C, Olmstead, Marilyn M, Mascal, Mark, Legese, Belete, Cho, Jae-Young, Beingessner, Rachel L, Yamazaki, Takeshi, Fenniri, Hicham
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Language:English
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Summary:N-substituted pyrido[4,3-d]pyrimidines are heterocycles which exhibit the asymmetric hydrogen bonding codes of both guanine and cytosine at 60° 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 Å 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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo4019792