Pyrolytic and gas phase fullerene derivatization reactions

Steven H. Hoke, Jay Molstad, Bart Kahr, R. Graham Cooks

Research output: Contribution to journalArticle

Abstract

The bulk production of naphthyne derivatives of [60]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 languageEnglish (US)
Pages (from-to)209-219
Number of pages11
JournalInternational Journal of Mass Spectrometry and Ion Processes
Volume138
Issue numberC
DOIs
StatePublished - Oct 13 1994

Keywords

  • Chemical ionization
  • Cycloaddition
  • Fullerenes
  • Pyrolytic reaction

ASJC Scopus subject areas

  • Spectroscopy

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