Host-guest complexes of cucubit[8]uril with phenanthrolines and some methyl derivatives

The host-guest relationship between cucurbit[8]uril, phenanthrolines and some methyl substituted 1,10-phenanthrolines has been investigated by using 1H NMR spectroscopy and fluorescence spectroscopy. The results showed that phenanthrolines as molecular guests bind in the cavity and portal of cucurbit[8]uril in a ratio of 2:1 (guest to host). The phenanthroline isomers 1,10-,1,7- and 4,7- showed red shifts between 47 and 108 nm and pronounced increases in fluorescent intensity. These same isomers produced inclusion complexes with cucur-bit[8]uril which had moderate to fast exchange rates on the 1H NMR time scale. The methyl substituted 1,10-phenanthrolines studied gave stable inclusion complexes in a ratio of 2:1 which showed slow exchange rates. These guests formed п-п stacked pairs which were cavity bound but also partly protruded from only one portal forming unsymmetrical host-guest complexes. In addition, these п-п stacked pairs formed orientation isomers within the confines of the cucur-bit[8]uril cavity.

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