The bulk production of naphthyne derivatives of fullerene, C60, is achieved by pyrolysis of 1,8-diiodonaphthalene in the presence of C60. Desorption chemical ionization mass spectra, recorded in the negative ion mode, show the addition of up to ten naphthyne units to a single C60 molecule. Products containing two C60 molecules are also generated. Tandem mass spectrometry confirms that covalent bonding has occurred. Similar reactions are described for the reactive intermediates generated from 1,8-naphthalic anhydride, 9-iodoanthracene, 2,6-dimethoxyiodobenzene, 2-iodonaphthalene and hexabromobenzene. Evidence for a [4 + 2] Diels-Alder ion/molecule reaction between mass-selected fullerene cations and methoxy-substituted 1,3-butadienes is presented. Ion/molecule reactions of various closed shell cations derived from the dissociative electron ionization of chlorine containing compounds are shown to result in the methylation, acylation, phenylation and benzylation of fullerenes in the course of positive ion chemical ionization. In the negative ion mode, halogenated fullerene anions are observed. At high desorption temperatures, the addition of at least 30 hydrogen atoms to C60 is reported.
|Original language||English (US)|
|Number of pages||11|
|Journal||International Journal of Mass Spectrometry and Ion Processes|
|State||Published - Oct 13 1994|
- Chemical ionization
- Pyrolytic reaction
ASJC Scopus subject areas