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

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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

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Citation Formats

A. DURMUS et al., “Synthesis of N-substituted Pyrido[4,3-d]pyrimidines for the Large-Scale Production of Self-Assembled Rosettes and Nanotubes,” JOURNAL OF ORGANIC CHEMISTRY, pp. 11421–11426, 2013, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/40430.