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Journal of the Mexican Chemical Society

versión impresa ISSN 1870-249X

J. Mex. Chem. Soc vol.53 no.3 México jul./sep. 2009

 

Article

 

Towards the Stepwise Assembly of Molecular Borromean Rings. A Donor–Acceptor Ring–in–Ring Complex*

 

Ross S. Forgan, Jason M. Spruell, John–Carl Olsen, Charlotte L. Stern and J. Fraser Stoddart*

 

Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208, USA. Tel: +1–847–491–3793, Fax: +1–847–491–1009,*Responsible author: stoddart@northwestern.edu, Web: http://stoddart.northwestern.edu.

 

Received June 26, 2009
Accepted September 10, 2009

 

Abstract

The assembly of molecular Borromean Rings from constitutionally independent rings in a stepwise manner depends on the preparation of robust "ring–in–ring" complexes. The π–electron rich macrocycle bis–1,5–dinaphtho[50]crown–14 (1) is shown to form a donor–acceptor ring–in–ring complex with the π–electron poor cyclophane cyclobis(paraquat–4,4'–biphenylene) (24 + ) in solution. In the crystal superstructure of [12]·4PF6, CH···O interactions between the polyether loops of 1 and the bipyridinium units of 24 + could disfavor the threading of dialkylammonium components of a third ring.

Keywords: Borromean Rings; Ring–in–Ring Complex; Donor–Acceptor; Supramolecular Chemistry; Crystal Structure.

 

Resumen

El ensamblaje por pasos de Anillos Borromeos moleculares a partir de anillos constitucionalmente independientes depende de la preparación de complejos robustos "ring–in–ring". El macrociclo rico en electrones n bis–1,5–dinafto[50]corona–14 (1) forma en solución un complejo "ring–in–ring" donador–aceptor con el ciclofano pobre en electrones π ciclobis(paracuat–4,4'–bifenileno) (24+). En la superestructura cristalina de [12]·4PF6, las interacciones CH···O entre los lazos poliéteres de 1 y las unidades bipiridinio de 24 +pueden desfavorecer el enhebrado de componentes dialquilamonio de un tercer anillo.

Palabras clave: Anillos Borromeos; complejo "ring–in–ring"; donador–aceptor; Química Supramolecular; estructura cristalina.

 

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Acknowledgements

JMS gratefully acknowledges the National Science Foundation for a Graduate Research Fellowship and Northwestern University for a Presidential Fellowship. The authors wish to thank Dr Jennifer Seymour of the Northwestern Analytical Services Laboratory for her continued time and assistance with all aspects of mass spectrometry.

 

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Note

*Dedicated to the Memory of Ernest L. Eliel.