Self-Assembly of N3-Substituted Xanthines in the Solid State and at the Solid鈥揕iquid Interface

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• 作者：Artur Ciesielski ; S茅bastien Haar ; Attila B茅nyei ; G谩bor Paragi ; C茅lia Fonseca Guerra ; F. Matthias Bickelhaupt ; Stefano Masiero ; J谩nos Szolom谩jer ; Paolo Samor矛 ; Gian Piero Spada ; Lajos Kov谩cs
• 刊名：Langmuir
• 出版年：2013
• 出版时间：June 18, 2013
• 年：2013
• 卷：29
• 期：24
• 页码：7283-7290
• 全文大小：535K
• 年卷期：v.29,no.24(June 18, 2013)
• ISSN：1520-5827

文摘

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鈥搇iquid interface, corroborated by dispersion-corrected density functional theory (DFT) studies and X-ray diffraction.