Orientational isomers of α-cyclodextrin [2]semi-rotaxanes with asymmetric dicationic threads†
Abstract
Two series of novel dicationic threading molecules [Quin(CH2)10R]2+ and [3,5-Lut(CH2)10R]2+, where Quin+ = quinuclidinium, 3,5-Lut+ = 3,5-lutidinium, and R+ = N(CH3)3+ and N(CH3)2CH2CH3+, form [2]semi-rotaxanes with α-cyclodextrin (α-CD) in aqueous solution. The quinuclidinium and 3,5-lutidinium are sufficiently bulky to prevent threading while the R+ groups allow for slow threading by α-CD at 25 °C. The resulting [2]semi-rotaxanes exist in two orientational isomers owing to the asymmetry of both the α-CD cavity and the threading molecules. Two-dimensional