Reaction of thin films of solid-state benzene and pyridine with calcium

Dallas L. Matz, Matthew C. Schalnat, Jeanne E Pemberton

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The reaction between small organic molecules and low work function metals is of interest in organometallic, astronomical, and optoelectronic device chemistry. Here, thin, solid-state, amorphous benzene and pyridine films are reacted with Ca at 30 K under ultrahigh vacuum with the reaction progress monitored by Raman spectroscopy. Although both films react with Ca to produce product species identifiable by their vibrational spectroscopic signatures, benzene is less reactive with Ca than pyridine. Benzene reacts by electron transfer from Ca to benzene producing multiple species including the phenyl radical anion, the phenyl radical, and the benzyne diradical. Pyridine initially reacts along a similar electron transfer pathway as indicated by the presence of the corresponding pyridyl radical and pyridyne diradical species, but these pyridyl radicals are less stable and subject to further ring-opening reactions that lead to a complex array of smaller molecule reaction products and ultimately amorphous carbon. The elucidation of this reaction pathway provides insight into the reactions of aromatics with Ca that are relevant in the areas of catalysis, astrochemistry, and organic optoelectronics.

Original languageEnglish (US)
Pages (from-to)12989-12997
Number of pages9
JournalJournal of the American Chemical Society
Volume134
Issue number31
DOIs
StatePublished - Aug 8 2012

Fingerprint

Benzene
Pyridine
Calcium
Thin films
Optoelectronic devices
Electrons
Molecules
Raman Spectrum Analysis
Amorphous carbon
Ultrahigh vacuum
Organometallics
Vacuum
Catalysis
Reaction products
Anions
Raman spectroscopy
Negative ions
Carbon
Metals
Equipment and Supplies

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Reaction of thin films of solid-state benzene and pyridine with calcium. / Matz, Dallas L.; Schalnat, Matthew C.; Pemberton, Jeanne E.

In: Journal of the American Chemical Society, Vol. 134, No. 31, 08.08.2012, p. 12989-12997.

Research output: Contribution to journalArticle

Matz, Dallas L. ; Schalnat, Matthew C. ; Pemberton, Jeanne E. / Reaction of thin films of solid-state benzene and pyridine with calcium. In: Journal of the American Chemical Society. 2012 ; Vol. 134, No. 31. pp. 12989-12997.
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