Putting Ammonia into a Chemically Opened Fullerene

We put ammonia into an open-cage fullerene with a 20-membered ring (1) as the orifice and examined the properties of the complex using NMR and MALDI-TOF mass spectroscopy. The proton NMR shows a broad resonance corresponding to endohedral NH3 at δH = −12.3 ppm relative to TMS. This resonance was seen to narrow when a 14N decoupling frequency was applied. MALDI spectroscopy confirmed the presence of both 1 (m/z = 1172) and 1 + NH3 (m/z = 1189), and integrated intensities of MALDI peak trains and NMR resonances indicate an incorporation fraction of 35−50% under our experimental conditions. NMR observations showed a diminished incorporation fraction after 6 months of storage at −10 °C, which indicates that ammonia slowly escapes from the open-cage fullerene.