title: Self-assembly of N3-substituted xanthines in the solid state and at the solid-liquid interface.
abstract: The self-assembly of small molecular modules interacting through noncovalent forces is increasingly being used to generate functional structures and materials for electronic, catalytic, and biomedical applications. The greatest control over the geometry in H-bond supramolecular architectures, especially in H-bonded supramolecular polymers, can be achieved by exploiting the rich programmability of artificial nucleobases undergoing self-assembly through strong H bonds. Here N(3)-functionalized xanthine modules are described, which are capable of self-associating through self-complementary H-bonding patterns to form H-bonded supramolecular ribbons. The self-association of xanthines through directional H bonding between neighboring molecules allows the controlled generation of highly compact 1D supramolecular polymeric ribbons on graphite. These architectures have been characterized by scanning tunneling microscopy at the solid-liquid interface, corroborated by dispersion-corrected density functional theory (DFT) studies and X-ray diffraction.
authors.affiliation: Nanochemistry Laboratory, ISIS & icFRC, Université de Strasbourg & CNRS, Strasbourg, France.
authors.forename: Artur
authors.initials: A
authors.lastname: Ciesielski
authors.forename: Sébastien
authors.initials: S
authors.lastname: Haar
authors.forename: Attila
authors.initials: A
authors.lastname: Bényei
authors.forename: Gábor
authors.initials: G
authors.lastname: Paragi
authors.forename: Célia Fonseca
authors.initials: CF
authors.lastname: Guerra
authors.forename: F Matthias
authors.initials: FM
authors.lastname: Bickelhaupt
authors.forename: Stefano
authors.initials: S
authors.lastname: Masiero
authors.forename: János
authors.initials: J
authors.lastname: Szolomájer
authors.forename: Paolo
authors.initials: P
authors.lastname: Samorì
authors.forename: Gian Piero
authors.initials: GP
authors.lastname: Spada
authors.forename: Lajos
authors.initials: L
authors.lastname: Kovács
mesh_terms: D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008962:Models, Theoretical; D014970:Xanthines / Q000737:chemistry*
chemical_list: D014970:Xanthines