Rotaxanes 3 , amide-type

Fig. 2 Template syntheses of rotaxanes the Cu(I) ion binds a phenanthroline ligand inside a macrocycle (top left). A l f5-paraquat macrocycle is clipped around an axle bearing a hydroquinone center piece (top right). Hydrogen bonding permits the use of nonionic template effects for the preparation of amide-type rotaxanes (bottom left). Phenolate anions bound to the macrocycle react as a supramolecular nucleophile (bottom right).

A successful synthesis of a rotaxane of this type is shown in Figure 5. First, one tiityl aniline stopper is reacted with the terephthaloyl chloride to from semiaxle 9. This semiaxle threads into the tetralactam macrocycle 3 and is held by the amide template. Then, the preorganized complex is reacted with the second stopper 11 to yield rotaxane 12. Figure 5 shows three hydrogen bonds to form, which is in accord with AMI calculations on this system [19] and X-Ray crystal structure analysis [22],... 

Fig. 12 Examples of the use of color in depictions of various types of MIMs. Note how the colors and positions of constituent parts in the three-dimensional structures reflect those in the structural drawings to enhance clarity between representations of (a) a donor-acceptor [2]catenane [75] and (b) an ammonium-binding [2]rotaxane [76] from our group, (c) a transition metal-templated Solomon Knot from the Sauvage and Fujita groups [77], and (d) a benzylic amide [2]catenane from the Leigh group [78]. Reproduced with permission from [75] (copyright 1991 Royal Society of Chemistry), [76] (copyright 2000 Wiley-VCH), [77] (copyright 1999 Royal Society of Chemistry), [78] (copyright 1995 Wiley-VCH)...

New catenane (cf. 17) and rotaxane (cf. 20) types have been obtained via supramolecular template syntheses The amide-based interlocked structures can be designed by appropriate choice of building units (cf. 13, 14) to form stable out/out, in/in and in/out isomers (cf. 17a, 17b), which can be separated [19]. It can be demonstrated that one of the two macromonocycles (cf. 15) of the... 

A further type of threading is involved in amide (pseudo)rotaxanes. In this class of compounds both components are amides (e.g. L1097 with L1098 Eq. 4.64) [204]. There are many sites for hydrogen-bonding and n-n (stacking, donor-acceptor) non-covalent interactions between the components [205]. 

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