An Open‐Cage Fullerene That Mimics the C60H10 (5, 5)‐Carbon Nanotube Endcap to Host Acetylene and Hydrogen Cyanide Molecules. Issue 46 (5th October 2016)

• Record Type: Journal Article
• Authors: Chen, Chi‐Shian; Yeh, Wen‐Yann
• Is Part Of: Chemistry. Volume 22:Issue 46(2016)
• Page Start: 16425
• Page End: 16428
• Publication Date: 2016-10-05
• Subjects: cage compounds -- fullerenes -- host–guest systems -- nanotubes -- structure elucidation; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201604114
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Treatment of the open‐cage fullerene C63 H4 NO2 (Ph)2 (Py)(N2 C6 H4 ) (1 ) with methanol at 150 °C results in an orifice‐enlargement reaction to give C69 H8 NO(CO2 Me)(Ph)(Py)(N2 C6 H4 ) (2 ). The overall yield from C60 to isolated2 is 6.1 % (four steps). Compound2 contains a 24‐membered elliptic orifice that spans 8.45 Å along the major axis and 6.37 Å along the minor axis. The skeleton of2 resembles the hypothetic C60 H10 (5, 5)‐carbon nanotube endcap. The cup‐shaped structure of2 is able to include water, hydrogen cyanide, and acetylene, forming H2 O@2, HCN@2, and C2 H2 @2, respectively. The molecular structures of H2 O@2 and HCN@2 have been determined by X‐ray crystallography. The 1 H NMR spectra reveal substantial upfield shifts for the endohedral species, such as δ =−10.30 (for H2 O), −2.74 and −14.26 (for C2 H2 ), and −1.22 ppm (for HCN), owing to the strong shielding effects of the fullerene cage. Abstract : Capping it off : C69 H8 NO(CO2 Me)(Ph)(Py)(N2 C6 H4 ), a short, rim‐modified, quasi carbon nanotube has been prepared. It is able to include water, hydrogen cyanide, and acetylene, and the structures of the H2 O and HCN inclusion products were determined by X‐ray crystallography. Strong shielding effects from the fullerene cage are observed for the endohedral species ( δ =−1.22 to −14.26 ppm).