Self-assembly of N3-substituted xanthines in the solid state and at the solid-liquid interface

Artur Ciesielski, Sébastien Haar, Attila Bényei, Gábor Paragi, Célia Fonseca Guerra, F. Matthias Bickelhaupt, Stefano Masiero, János Szolomájer, Paolo Samorì, Gian Piero Spada, Lajos Kovács

Research output: Contribution to journalArticle

9 Citations (Scopus)


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 N3-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.

Original languageEnglish
Pages (from-to)7283-7290
Number of pages8
Issue number24
Publication statusPublished - Jun 18 2013

ASJC Scopus subject areas

  • Materials Science(all)
  • Condensed Matter Physics
  • Surfaces and Interfaces
  • Spectroscopy
  • Electrochemistry

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    Ciesielski, A., Haar, S., Bényei, A., Paragi, G., Guerra, C. F., Bickelhaupt, F. M., Masiero, S., Szolomájer, J., Samorì, P., Spada, G. P., & Kovács, L. (2013). Self-assembly of N3-substituted xanthines in the solid state and at the solid-liquid interface. Langmuir, 29(24), 7283-7290.