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

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• 作者：Asuman Durmus ; Gorkem Gunbas ; Steven C. Farmer ; Marilyn M. Olmstead ; Mark Mascal ; Belete Legese ; Jae-Young Cho ; Rachel L. Beingessner ; Takeshi Yamazaki ; Hicham Fenniri
• 刊名：Journal of Organic Chemistry
• 出版年：2013
• 出版时间：November 15, 2013
• 年：2013
• 卷：78
• 期：22
• 页码：11421-11426
• 全文大小：384K
• 年卷期：v.78,no.22(November 15, 2013)
• ISSN：1520-6904

文摘

N-substituted pyrido[4,3-d]pyrimidines are heterocycles which exhibit the asymmetric hydrogen bonding codes of both guanine and cytosine at 60掳 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 脜 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.