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Transition-Metal-Complexed Catenanes and Rotaxanes: From Dynamic Systems to Functional Molecular Machines

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Molecular Machines and Motors

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 354))

Abstract

Transition metal-based catenanes and rotaxanes constitute a specific class of mechanically interlocked molecules whose metal centers are essential both as templates in the construction of the compounds and for their ability to induce large-amplitude motions. In the present chapter we will first present a historical perspective of the field of interlocking compounds in general, in relation to molecular machines, starting with old work dating back to the 1980s and 1990s. Copper was shown many years ago to be the metal of choice for synthesizing the compounds via a template approach and for setting the molecules in motion using a redox signal (CuII/CuI). In a second paragraph, we will discuss various rotaxanes able to undergo a pirouetting motion of the axis within the threaded ring. Two families of such molecules will be mentioned: (1) a porphyrin-containing [2]rotaxane whose pirouetting motion is induced by a chemical reaction and (2) electrochemically driven systems. In this second category of [2]rotaxanes, the rate of motion could be dramatically increased by gradually modifying structural parameters and, in particular, by making the metal center less and less hindered by its surrounding ligands. The third section will be devoted to molecular shuttles and muscles, both families of compounds being reminiscent of linear machines such as biological muscles. By replacing the classical 2,9-diaryl-1,10-phenanthroline chelate (highly shielding and hindering) used by our group since the 1980s by an endocyclic but non-sterically hindering 3,3′-biisoquinoline derivative, the shuttling rate was increased in spectacular fashion, demonstrating the importance of steric factors in transition metal-based molecular machines. The same 3,3′-biisoquinoline motif was also used in the elaboration of a three-station shuttle, leading to long-distance (>20 Å) transport of a ring along the axis on which it is threaded. Finally, porphyrin-containing [3]rotaxanes and [4]rotaxanes, the latter displaying an overall cyclic structure, will be discussed and shown to behave as adjustable and switchable receptors. The synthesis of such compounds is a particularly challenging task in itself. In addition, the new receptors display fascinating properties such as, in particular, their ability to compress various guests and to expel them from their binding site using a chemical signal.

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Abbreviations

bipy:

2,2′-Bipyridyl

CN:

Coordination number

CPK:

Corey–Pauling–Koltun

DABCO:

1,4-Diazabicyclo[2.2.2]octane

DOSY:

Diffusion-ordered NMR spectroscopy

dpbiiq:

8,8′-Diphenyl-3,3′-biisoquinoline fragment

dpp:

2,9-Diphenyl-1,10-phenanthroline

phen:

1,10-Phenanthroline

terpy:

2,2′,6′,2″-Terpyridine

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Acknowledgments

We would like to thank the highly talented students and postdoctoral researchers who participated in the work discussed in the present chapter. Their respective contributions have been essential to the success of our projects in terms of experimental work but also for their ideas and suggestions regarding the design of the systems and the synthesis routes expected to afford the target molecules.

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Authors and Affiliations

  1. Institut de Chimie de Strasbourg, Université de Strasbourg, 4, rue Blaise Pascal, Strasbourg, 67070, France

    Stéphanie Durot, Valérie Heitz & Angélique Sour

  2. Institut de Science et Ingénierie Supramoléculaires, Université de Strasbourg, 8, Allée Gaspard Monge, Strasbourg, 67000, France

    Jean-Pierre Sauvage

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  1. Stéphanie Durot
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  2. Valérie Heitz
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  3. Angélique Sour
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  4. Jean-Pierre Sauvage
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Correspondence to Jean-Pierre Sauvage .

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Editors and Affiliations

  1. Dept. of Chemistry “Giacomo Ciamician”, University of Bologna, Bologna, Italy

    Alberto Credi

  2. Dept. of Chemistry “Giacomo Ciamician”, University of Bologna, Bologna, Germany

    Serena Silvi

  3. Dept. of Chemistry “Giacomo Ciamician", University of Bologna, Bologna, Italy

    Margherita Venturi

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Durot, S., Heitz, V., Sour, A., Sauvage, JP. (2014). Transition-Metal-Complexed Catenanes and Rotaxanes: From Dynamic Systems to Functional Molecular Machines. In: Credi, A., Silvi, S., Venturi, M. (eds) Molecular Machines and Motors. Topics in Current Chemistry, vol 354. Springer, Cham. https://doi.org/10.1007/128_2013_514

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