Solvent exchange in thermally stable resorcinarene nanotubes |
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Authors: | Mansikkamäki Heidi Busi Sara Nissinen Maija Ahman Antti Rissanen Kari |
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Affiliation: | NanoScience Center, Department of Chemistry, Laboratory of Organic Chemistry, University of Jyv?skyl?, PO Box 35, 40014 JYU, Finland. |
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Abstract: | The assembly of C-methyl resorcinarene into a tubular supramolecular solid-state structure, its thermal stability, and its hosting properties are reported. Careful control of the crystallisation conditions of C-methyl resorcinarene and 1,4-dimethyl-1,4-diazoniabicyclo[2.2.2]octane (1,4-dimethyl DABCO) dibromide leads to a formation of two crystallographically different, but structurally very similar, solid-state nanotube structures. These structures undergo a remarkable variety of supramolecular interactions, which lead to the formation of 0.5 nm diameter nonpolar tubes through the crystal lattice. The formation of these tubes is templated by suitably sized small alcohols, namely, n-propanol, 2-propanol, or n-butanol. The self-assembly involves close pi...pi interactions between the adjacent resorcinarenes, and C--H...pi and cation...pi interactions between the resorcinarenes and the guest 1,4-dimethyl DABCO dications. The crystals of these supramolecular tube structures are thermally very stable and the included solvent alcohol can be removed from the tubes without breaking the single-crystalline structure of the assembly. After removal of the solvent molecules the tubes can be filled with other small, less polar solvent molecules such as dichloromethane. |
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Keywords: | crystal engineering host–guest systems nanotubes resorcinarenes supramolecular chemistry |
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