Abstract
The templated clipping of a ferrocene-grafted isophthalic acid derivative to encircle a hydrogen-bonding axle through the reaction with 1,4-bis(aminomethyl)benzene is described. The constituent electroactive macrocycle of the resultant [2]rotaxane is a homologue of the versatile benchmark tetraamide variant developed by Leigh and co-workers. The relative templating effect of different hydrogen-bonding motifs in rotaxane and pseudorotaxane generation is compared, with yields varying from 0 to 41%. The electrochemical properties and single crystal X-ray structure of a doubly ferrocene-decorated [2]rotaxane are further reported.
Highlights
The development of interlocked molecules with tailored properties allowed the preparation of molecular machines able to perform several functions as artificial molecular switches [1]
The highly efficient rotaxane formation developed by Leigh allowed the generation of a tetraamide macrocycle on a fumaramide or succinamide thread in high yields
We report the synthesis of a rotaxane, where a “clipping” reaction generates a tetraamide macrocycle with two peripheral ferrocene moieties on a preformed thread (Figure 1b)
Summary
The development of interlocked molecules with tailored properties allowed the preparation of molecular machines able to perform several functions as artificial molecular switches [1]. The highly efficient rotaxane formation developed by Leigh allowed the generation of a tetraamide macrocycle on a fumaramide or succinamide thread in high yields This methodology consisted of a 4-component macrocyclization reaction, templated by the thread to obtain the corresponding interlocked molecule (Figure 1a) [4,5]. This class of macrocycle has proved extremely versatile, having given rise to a wealth of functional architectures [6,7,8,9,10,11,12,13,14].
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