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Solvent Exchange in Thermally Stable Resorcinarene Nanotubes
Author(s) -
Mansikkamäki Heidi,
Busi Sara,
Nissinen Maija,
Åhman Antti,
Rissanen Kari
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200501201
Subject(s) - resorcinarene , dabco , supramolecular chemistry , chemistry , solvent , octane , molecule , thermal stability , crystal structure , crystallography , organic chemistry
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 π ⋅⋅⋅ π interactions between the adjacent resorcinarenes, and CH ⋅⋅⋅ π and cation ⋅⋅⋅ π 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.