{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,22]],"date-time":"2025-11-22T23:00:36Z","timestamp":1763852436604,"version":"build-2065373602"},"reference-count":60,"publisher":"Wiley","issue":"46","license":[{"start":{"date-parts":[[2016,10,5]],"date-time":"2016-10-05T00:00:00Z","timestamp":1475625600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2016,11,7]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Treatment of the open\u2010cage fullerene C<jats:sub>63<\/jats:sub>H<jats:sub>4<\/jats:sub>NO<jats:sub>2<\/jats:sub>(Ph)<jats:sub>2<\/jats:sub>(Py)(N<jats:sub>2<\/jats:sub>C<jats:sub>6<\/jats:sub>H<jats:sub>4<\/jats:sub>) (<jats:bold>1<\/jats:bold>) with methanol at 150\u2009\u00b0C results in an orifice\u2010enlargement reaction to give C<jats:sub>69<\/jats:sub>H<jats:sub>8<\/jats:sub>NO(CO<jats:sub>2<\/jats:sub>Me)(Ph)(Py)(N<jats:sub>2<\/jats:sub>C<jats:sub>6<\/jats:sub>H<jats:sub>4<\/jats:sub>) (<jats:bold>2<\/jats:bold>). The overall yield from C<jats:sub>60<\/jats:sub> to isolated <jats:bold>2<\/jats:bold> is 6.1\u2009% (four steps). Compound <jats:bold>2<\/jats:bold> contains a 24\u2010membered elliptic orifice that spans 8.45\u2005\u00c5 along the major axis and 6.37\u2005\u00c5 along the minor axis. The skeleton of <jats:bold>2<\/jats:bold> resembles the hypothetic C<jats:sub>60<\/jats:sub>H<jats:sub>10<\/jats:sub> (5,5)\u2010carbon nanotube endcap. The cup\u2010shaped structure of <jats:bold>2<\/jats:bold> is able to include water, hydrogen cyanide, and acetylene, forming H<jats:sub>2<\/jats:sub>O@<jats:bold>2<\/jats:bold>, HCN@<jats:bold>2<\/jats:bold>, and C<jats:sub>2<\/jats:sub>H<jats:sub>2<\/jats:sub>@<jats:bold>2<\/jats:bold>, respectively. The molecular structures of H<jats:sub>2<\/jats:sub>O@<jats:bold>2<\/jats:bold> and HCN@<jats:bold>2<\/jats:bold> have been determined by X\u2010ray crystallography. The <jats:sup>1<\/jats:sup>H\u2005NMR spectra reveal substantial upfield shifts for the endohedral species, such as <jats:italic>\u03b4<\/jats:italic>=\u221210.30 (for H<jats:sub>2<\/jats:sub>O), \u22122.74 and \u221214.26 (for C<jats:sub>2<\/jats:sub>H<jats:sub>2<\/jats:sub>), and \u22121.22\u2005ppm (for HCN), owing to the strong shielding effects of the fullerene cage.<\/jats:p>","DOI":"10.1002\/chem.201604114","type":"journal-article","created":{"date-parts":[[2016,9,12]],"date-time":"2016-09-12T03:33:16Z","timestamp":1473651196000},"page":"16425-16428","source":"Crossref","is-referenced-by-count":25,"title":["An Open\u2010Cage Fullerene That Mimics the C<sub>60<\/sub>H<sub>10<\/sub> (5,5)\u2010Carbon Nanotube Endcap to Host Acetylene and Hydrogen Cyanide Molecules"],"prefix":"10.1002","volume":"22","author":[{"given":"Chi\u2010Shian","family":"Chen","sequence":"first","affiliation":[{"name":"Department of Chemistry National Sun Yat-Sen University  Kaohsiung 804 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