title: Synthesis of N-substituted pyrido[4,3-d]pyrimidines for the large-scale production of self-assembled rosettes and nanotubes.
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.
authors.affiliation: Department of Chemistry, University of California Davis , 1 Shields Avenue, Davis, California 95616, United States.
authors.forename: Asuman
authors.initials: A
authors.lastname: Durmus
authors.forename: Gorkem
authors.initials: G
authors.lastname: Gunbas
authors.forename: Steven C
authors.initials: SC
authors.lastname: Farmer
authors.forename: Marilyn M
authors.initials: MM
authors.lastname: Olmstead
authors.forename: Mark
authors.initials: M
authors.lastname: Mascal
authors.forename: Belete
authors.initials: B
authors.lastname: Legese
authors.forename: Jae-Young
authors.initials: JY
authors.lastname: Cho
authors.forename: Rachel L
authors.initials: RL
authors.lastname: Beingessner
authors.forename: Takeshi
authors.initials: T
authors.lastname: Yamazaki
authors.forename: Hicham
authors.initials: H
authors.lastname: Fenniri
mesh_terms: D018360:Crystallography, X-Ray; D003596:Cytosine / Q000737:chemistry; D006147:Guanine / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006860:Hydrogen Bonding; D008958:Models, Molecular; D015394:Molecular Structure; D043942:Nanotubes / Q000737:chemistry*; D010316:Particle Size; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry; D013499:Surface Properties
chemical_list: D006571:Heterocyclic Compounds; D011743:Pyrimidines; D006147:Guanine; D003596:Cytosine