Pyridine-appended 5,6-open-aza[60]fulleroid can act as a unique host for alcohols

Pyridine-appended 5,6-open-aza[60]fulleroid (2) and 6,6-closed-aza[60]fulle rene (3) were synthesised for the first time. It was found that 2, in which the aza group conjugates with the [60]fulleroid pi-system, can bind certai n alcohols via a hydrogen-bonding interaction and shows high selectivity to wards methanol. In contrast, 3, in which the aza group does not conjugate w ith the [60]fullerene pi-system, scarcely shows such an alcohol affinity. T he results indicate that a slight difference in the arrangement of the nitr ogens results in a drastic change in the guest affinity. The guest-binding processes were thoroughly investigated by UV-Vis absorption and NMR spectro scopic methods and electrochemical methods. This is a unique neutral guest recognition system utilising the [60]fullerene surface.