MASCAL RESEARCH GROUP

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NEWS AND HIGHLIGHTS

EXTERNAL LINKS

Sandwich complexation in cylindrophanes. 

The term cylindrophane refers to a series of sym-[5.5.5]heterocyclophanes which we designed and synthesized for the purpose of making novel benzene sandwich-type inclusion complexes.  The first were oxa- and azacylindrophanes, the latter of which form dynamic facial complexes with Ag(I) and Cu(I) by a combination of M–N and η¹ interactions with the benzene rings.  Interestingly, the metal precesses from one symmetry-related face of the cyclophane to the next at a rate that is metal-dependent (fast for Ag, slow for Cu).  The analogous thiacylindrophane forms sandwiches with these metals, leading to the first ever reports of Ag(I) and Cu(I) bis-η⁶ complexation.  The selectivity of the thiacylindrophane host for Ag(I) and Cu(I) was also remarkable, due to the unusual affinity of these metals for π donors. 

 

 

The complete inversion of the electronic nature of the cylindrophane, from electron rich transition metal host to electron deficient anion host, has been the latest drive in this project, and has led to the synthesis of a highly selective fluoride receptor based on ion-pair reinforced hydrogen bonds and anion-π interactions.  We are currently employing the cylindrophane-fluoride receptor as the basis for novel tracer probes for positron emission tomography.

 

 

Lead references:

 

"Design, Synthesis and Metal Binding Properties of a Mixed-donor Macrocycle."  M. Mascal, J. Hansen, A. J. Blake, W.-S. Li, Chem. Commun. 1998, 355.

 

"S-Cylindrophanes: From Metal Tweezers to Metal Sandwiches."  M. Mascal, J.-L. Kerdelhué, A. J. Blake, P. A. Cooke, Angew. Chem. Int. Ed. 1999, 38, 1968.

 

"On the Nature of Arene η⁶ Interactions in the Solid State and the Use of Cylindrophanes as Ligands for Sandwich Complexation of Metals with Longer-Range Interactions with the Benzene Ring."  M. Mascal, J.-L. Kerdelhué, A. J. Blake, P. A. Cooke, R. J. Mortimer, S. J. Teat, Eur. J.Inorg. Chem., 2000, 485.

 

"Fluoride-Selective Host Based on Anion-π Interactions, Ion Pairing and Hydrogen Bonding: Synthesis and Fluoride Ion Sandwich Complex."  M. Mascal, I. Yakovlev, E. B. Nikitin, J. C. Fettinger, Angew. Chem. Int. Ed. 2007, 46, 8782.