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.

Artur Ciesielski, Sébastien Haar, Attila Bényei, Gábor Paragi, Célia Fonseca Guerra, F. Matthias Bickelhaupt, et al. (2013). Self-Assembly of N3-Substituted Xanthines in the Solid State and at the Solid–Liquid Interface. LANGMUIR, 29, 7283-7290 [10.1021/la304540b].

Self-Assembly of N3-Substituted Xanthines in the Solid State and at the Solid–Liquid Interface

MASIERO, STEFANO;SPADA, GIAN PIERO;
2013

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 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.
2013
Artur Ciesielski, Sébastien Haar, Attila Bényei, Gábor Paragi, Célia Fonseca Guerra, F. Matthias Bickelhaupt, et al. (2013). Self-Assembly of N3-Substituted Xanthines in the Solid State and at the Solid–Liquid Interface. LANGMUIR, 29, 7283-7290 [10.1021/la304540b].
Artur Ciesielski;Sébastien Haar;Attila Bényei;Gábor Paragi;Célia Fonseca Guerra;F. Matthias Bickelhaupt;Stefano Masiero;János Szolomájer;Paolo Samorì;...espandi
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/191822
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