Encapsulation of Formaldehyde and Hydrogen Cyanide in an Open-Cage Fullerene.
Reaction of C63 NO2 (Ph)2 (Py) (1) with o-phenylenediamine and pyridine produces a mixture of C63 H4 NO2 (Ph)2 (Py)(N2 C6 H4 ) (2) and H2 O@2. Compound 2 is a new open-cage fullerene containing a 20-membered heterocyclic orifice, which has been fully characterized by NMR spectroscopy, high-resolution mass spectrometry, and X-ray crystallography. The elliptical orifice of 2 spans 7.45 Å along the major axis and 5.62 Å along the minor axis, which is large enough to trap water and small organic molecules. Thus, heating a mixture of 2 and H2 O@2 with hydrogen cyanide and formaldehyde in chlorobenzene affords HCN@2 and H2 CO@2, respectively. The (1) H NMR spectroscopy reveals substantial upfield shifts for the endohedral species (δ=-1.30 to -11.30 ppm), owing to the strong shielding effect of the fullerene cage.
Department of Chemistry, National Sun Yat-Sen University, Kaohsiung, 804, Taiwan.
Chi-Shian
CS
Chen
Instrumentation Center, National Taiwan Normal University, Taipei, 106, Taiwan.
Ting-Shen
TS
Kuo
Department of Chemistry, National Sun Yat-Sen University, Kaohsiung, 804, Taiwan. wenyann@mail.nsysu.edu.tw.
Wen-Yann
WY
Yeh
cage compounds; fullerenes; host-guest systems; inclusion compounds; structure elucidation