Encapsulation of Formaldehyde and Hydrogen Cyanide in an Open‐Cage Fullerene. Issue 26 (12th May 2016)

• Record Type: Journal Article
• Authors: Chen, Chi‐Shian; Kuo, Ting‐Shen; Yeh, Wen‐Yann
• Is Part Of: Chemistry. Volume 22:Issue 26(2016)
• Page Start: 8773
• Page End: 8776
• Publication Date: 2016-05-12
• Subjects: cage compounds -- fullerenes -- host–guest systems -- inclusion compounds -- structure elucidation; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201601737
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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 . Compound2 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 of2 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 of2 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. Abstract : It's a trap ! Organic compounds bearing a C=O or C≡N functional group are inserted into the new open‐cage fullerene C63 H4 NO2 (Ph)2 (Py)(N2 C6 H4 ) containing a 20‐membered ring orifice. 1 H NMR spectroscopy reveals substantial upfield shifts for the endohedral species owing to the strong shielding effect of the fullerene cage.