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Template-Directed Synthesis of a Rotacatenane

1999; Wiley; Volume: 1999; Issue: 6 Linguagem: Inglês

10.1002/(sici)1099-0690(199906)1999

1434-193X

David B. Amabilino, Peter R. Ashton, José A. Bravo, Françisco M. Raymo, J. Fraser Stoddart, Andrew J. P. White, David J. Williams,

Crystallography and molecular interactions

A [2]catenane, able to bind π-electron-rich guests inside the cavity of one of its two macrocyclic components has been designed and synthesized using supramolecular assistance. This recognition motif has been exploited to template the formation of a so-called rotacatenane – i.e., a molecule composed of a dumbbell-shaped component threaded through the cavity of one of the two mechanically interlocked macrocyclic components of a [2]catenane. The structure of this [2]catenane, as well as that of a model [2]catenane, have been characterized unequivocally by single-crystal X-ray analyses. Furthermore, some of the co-conformational changes associated with these mechanically interlocked molecules in solution have been probed by variable-temperature 1H-NMR spectroscopy.