{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,15]],"date-time":"2025-10-15T17:40:04Z","timestamp":1760550004005,"version":"build-2065373602"},"reference-count":71,"publisher":"Wiley","issue":"26","license":[{"start":{"date-parts":[[2016,5,12]],"date-time":"2016-05-12T00:00:00Z","timestamp":1463011200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100004663","name":"Ministry of Science and Technology of Taiwan","doi-asserted-by":"crossref","id":[{"id":"10.13039\/501100004663","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2016,6,20]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Reaction of C<jats:sub>63<\/jats:sub>NO<jats:sub>2<\/jats:sub>(Ph)<jats:sub>2<\/jats:sub>(Py) (<jats:bold>1<\/jats:bold>) with <jats:italic>o\u2010<\/jats:italic>phenylenediamine and pyridine produces a mixture of 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>2<\/jats:bold>) and H<jats:sub>2<\/jats:sub>O@<jats:bold>2<\/jats:bold>. Compound <jats:bold>2<\/jats:bold> is a new open\u2010cage fullerene containing a 20\u2010membered heterocyclic orifice, which has been fully characterized by NMR spectroscopy, high\u2010resolution mass spectrometry, and X\u2010ray crystallography. The elliptical orifice of <jats:bold>2<\/jats:bold> spans 7.45\u2005\u00c5 along the major axis and 5.62\u2005\u00c5 along the minor axis, which is large enough to trap water and small organic molecules. Thus, heating a mixture of <jats:bold>2<\/jats:bold> and H<jats:sub>2<\/jats:sub>O@<jats:bold>2<\/jats:bold> with hydrogen cyanide and formaldehyde in chlorobenzene affords HCN@<jats:bold>2<\/jats:bold> and H<jats:sub>2<\/jats:sub>CO@<jats:bold>2<\/jats:bold>, respectively. The <jats:sup>1<\/jats:sup>H\u2005NMR spectroscopy reveals substantial upfield shifts for the endohedral species (<jats:italic>\u03b4<\/jats:italic>=\u22121.30 to \u221211.30\u2005ppm), owing to the strong shielding effect of the fullerene cage.<\/jats:p>","DOI":"10.1002\/chem.201601737","type":"journal-article","created":{"date-parts":[[2016,4,28]],"date-time":"2016-04-28T10:56:55Z","timestamp":1461841015000},"page":"8773-8776","source":"Crossref","is-referenced-by-count":36,"title":["Encapsulation of Formaldehyde and Hydrogen Cyanide in an Open\u2010Cage Fullerene"],"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 Taiwan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ting\u2010Shen","family":"Kuo","sequence":"additional","affiliation":[{"name":"Instrumentation Center National Taiwan Normal University  Taipei 106 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