Pyridine-appended 5,6-open-azafulleroid (2) and 6,6-closed-azafullerene (3) were synthesised for the first time. It was found that 2, in which the aza group conjugates with the fulleroid π-system, can bind certain alcohols via a hydrogen-bonding interaction and shows high selectivity towards methanol. In contrast, 3, in which the aza group does not conjugate with the fullerene π-system, scarcely shows such an alcohol affinity. The results indicate that a slight difference in the arrangement of the nitrogens results in a drastic change in the guest affinity. The guest-binding processes were thoroughly investigated by UV-Vis absorption and NMR spectroscopic methods and electrochemical methods. This is a unique neutral guest recognition system utilising the fullerene surface.
|Number of pages||4|
|Journal||Journal of the Chemical Society. Perkin Transactions 2|
|Publication status||Published - Feb 2000|
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