Multipoint recognition of ditopic aromatic guest molecules via Ag-π interactions within a dimetal macrocycle

J Am Chem Soc. 2014 Dec 31;136(52):17946-9. doi: 10.1021/ja5106249. Epub 2014 Dec 16.


A macrocyclic host molecule possessing a nanocavity with two Ag(I) centers for guest binding and four anthracene walls has been developed. This dimetal-macrocycle forms stable inclusion complexes with ditopic aromatic guest molecules, [2.2]paracyclophane, and ferrocene, in solution and/or in the solid state through Ag-π interactions within the nanocavity. The binding constants for the inclusion complexes were found to range roughly from 10(4) to 10(9) M(-1). Electrochemical measurement revealed that the oxidized form of the included cationic ferrocene was less stabilized due to the direct binding to the cationic two Ag(I) centers.