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Crystalline Self-Assembly of a Bowl-Like Cyclotriguaiacylene Derivative with Alcohol/Phenols by Hydrogen Bonding and C-H center dot center dot center dot pi Interactions: The Self-Inclusion Extended Organic Frameworks
Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
2010 (English)In: Crystal Growth & Design, ISSN 1528-7483, E-ISSN 1528-7505, Vol. 10, no 1, 314-320 p.Article in journal (Refereed) Published
Abstract [en]

Bowl-like tris-[(N-methyl-2-imidazoyl)]methoxy]cyclotriguaiacyclene (TMIM-CTG) (1) was synthesized and cocrystallized with ethanol, resorcinol, and phloroglucinol to afford three molecular complexes (TMIM-CTG)-(ethanol)(3) (2), (TMIM-CTG)-(resorcinol)-(CH3CN)(2) (3), and (TMIM-CTG)-(phloroglucinol)center dot(CH3CN)(2) (4), whose Structures have been determined by X-ray single crystal analysis. Except for the hydrogen bonds between imidazole of 1 and the hydroxyl group of alcohol/phenols (O-H center dot center dot center dot N), all crystals contain self-inclusion motifs with cooperative C-H center dot center dot center dot pi, interactions which can be considered as the secondary way to extend the primary hydrogen-bonded networks to (lie frameworks with higher levels. In complex 2. two adjacent TMIM-CTGs form a self-clasping dimer by an edge-to-face C-H center dot center dot center dot pi interaction between the imidazole ring and the benzene ring of CTG, which is further extended to a one-dimensional chain by the pi-pi. interactions between adjacent imidazole rings. The ethanol molecules interact with TMIM-CTGs by hydrogen bonding and fill channels within these chains. In complex 3, the self-assembly of TMIG-CTG and resorcinol Molecules by hydrogen bonding affords the Zigzag chain, which is then extended to the (4.4) sheet by the self-inclusion between TMIG-CTGs. Complex 4 contains a two-dimensional 4.8(2) hydrogen-bonding network betweenTMIG-CTG and phloroglucinol molecules, and the self-inclusion Of TMIG-CTGs extends it to,I novel three-dimensional supramolecular framework. The acetonitrile molecules in two latter Crystals arc included within the extended organic framework.

Place, publisher, year, edition, pages
2010. Vol. 10, no 1, 314-320 p.
Keyword [en]
CYCLOTRIVERATRYLENE-TYPE LIGANDS; CAMBRIDGE STRUCTURAL DATABASE; INORGANIC 3D NETWORKS; SOLID-STATE; RETICULAR CHEMISTRY; COORDINATION; CAPSULES; CRYPTOPHANES; COMPLEXES; MOLECULES
National Category
Chemical Sciences
Research subject
Materials Chemistry
Identifiers
URN: urn:nbn:se:su:diva-50057DOI: 10.1021/cg900905hISI: 000274757100049OAI: oai:DiVA.org:su-50057DiVA: diva2:382748
Note
authorCount :4Available from: 2011-01-03 Created: 2010-12-21 Last updated: 2017-12-11Bibliographically approved

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