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The first example of an oriented handcuff rotaxane has been obtained by through-the-annulus threading of a double-calix[6]arene system with a bis-ammonium axle. The relative orientation of the two calix-wheels can be predefined by exploiting the "endo-alkyl rule" which controls the directionality of the threading of alkylbenzylammonium axles with calixarene macrocycles.
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Ciao et al. (2013) studied this question.
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