Synthesis of N-substituted pyrido[4,3-d]pyrimidines for the large-scale production of self-assembled rosettes and nanotubes

Asuman Durmus, Gorkem Gunbas, Steven C. Farmer, Marilyn M. Olmstead, Mark Mascal, Belete Legese, Jae Young Cho, Rachel L. Beingessner, Takeshi Yamazaki, Hicham Fenniri

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Abstract

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.

Original languageEnglish (US)
Pages (from-to)11421-11426
Number of pages6
JournalJournal of Organic Chemistry
Volume78
Issue number22
DOIs
Publication statusPublished - Nov 15 2013

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Durmus, A., Gunbas, G., Farmer, S. C., Olmstead, M. M., Mascal, M., Legese, B., ... Fenniri, H. (2013). Synthesis of N-substituted pyrido[4,3-d]pyrimidines for the large-scale production of self-assembled rosettes and nanotubes. Journal of Organic Chemistry, 78(22), 11421-11426. https://doi.org/10.1021/jo4019792