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Threading of Conformationally Stable Calix[6]arene Wheels Substituted at the Methylene Bridges
Marina Tranfić Bakić1, Veronica Iuliano2, Carmen Talotta2
1Department of Chemistry and Biochemistry, Faculty of Food Technology and Biotechnology , University of Zagreb , Pierottijeva 6 , 10000 Zagreb , Croatia.
Abstract:
Calix[6]arenes disubstituted at the methylene bridges, which are stable in the cone or 1,2,3-alternate conformation, form pseudorotaxanes with dialkylammonium axles. The cone wheel-based pseudorotaxanes are 10-100 times more stable than those obtained with the native conformationally mobile calix[6]arene wheel, as a consequence of their higher degree of preorganization. The threading of conformationally stable 1,2,3-alternate calix[6]arenes is unprecedented in the literature. Therefore, very peculiar NMR features are here evidenced for this threading process involving the less symmetrical 1,2,3-alternate calix[6]arene conformation, which implies a peculiar rototranslation motion of the axle.
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