2010European Journal of Organic ChemistryRequires access

Synthesis of Fullerene‐Stoppered Rotaxanes Bearing Ferrocene Groups on the Macrocycle

Aurelio Mateo‐Alonso, Maurizio Prato

Open publisher page 22 citations

Abstract

Abstract The synthesis, characterisation and behaviour of a series of rotaxanes containing a fulleropyrrolidine stopper and two ferrocene moieties on the macrocycle is reported. Remarkably, the presence of large and bulky ferrocene groups does not interfere either in the synthesis or in the translocation of the macrocycle induced by π–π interactions between the macrocycle and the fullerene. The synthetic routes developed can also be applied to the preparation of rotaxane scaffolds that can be complexed to [Ru(CO)TPP] by axial coordination. Overall, the synthetic routes presented herein provide an efficient way to prepare a variety of rotaxanes and molecular shuttles with potential applications in different fields.

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Abstract The synthesis, characterisation and behaviour of a series of rotaxanes containing a fulleropyrrolidine stopper and two ferrocene moieties on the macrocycle is reported. Remarkably, the presence of large and bulky ferrocene groups does not interfere either in the synthesis or in the translocation of the macrocycle induced by π–π interactions between the macrocycle and the fullerene. The synthetic routes developed can also be applied to the preparation of rotaxane scaffolds that can be complexed to [Ru(CO)TPP] by axial coordination. Overall, the synthetic routes presented herein provide an efficient way to prepare a variety of rotaxanes and molecular shuttles with potential applications in different fields.

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Available abstract

Abstract The synthesis, characterisation and behaviour of a series of rotaxanes containing a fulleropyrrolidine stopper and two ferrocene moieties on the macrocycle is reported. Remarkably, the presence of large and bulky ferrocene groups does not interfere either in the synthesis or in the translocation of the macrocycle induced by π–π interactions between the macrocycle and the fullerene. The synthetic routes developed can also be applied to the preparation of rotaxane scaffolds that can be complexed to [Ru(CO)TPP] by axial coordination. Overall, the synthetic routes presented herein provide an efficient way to prepare a variety of rotaxanes and molecular shuttles with potential applications in different fields.

Key concepts: Ferrocene, Rotaxane, Chemistry, Fullerene, Molecular machine, Combinatorial chemistry, Stereochemistry, Nanotechnology

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