Electronic properties of pentacene versus triisopropylsilylethynyl- substituted pentacene: Environment-dependent effects of the silyl substituent

Olga Lobanova Griffith, John E. Anthony, Adolphus G. Jones, Dennis L. Lichtenberger

Research output: Contribution to journalArticle

74 Scopus citations

Abstract

Energy measures of the intra- and intermolecular electronic effects of triisopropylsilylethynyl substitution on pentacene have been obtained from the combination of closely related gas phase and solid phase ultraviolet photoelectron spectroscopy (UPS) measurements along with solution electrochemical measurements. The results show that the shift to lower ionization energy that is expected with this substitution and observed in the gas phase measurements becomes negligible in solution and is even reversed in the solid phase. The principles that emerge from this analysis are supported by electronic structure calculations at the density functional theory level. The relation between the gas phase and solid phase UPS measurements illustrated here provides a general approach to investigating the electronic effects acting on molecules in the condensed phase, which in this case are greater than the direct substituent electronic effects within the molecule. Electronic properties such as lower ionization energies built into the single-molecule building blocks of materials and devices may be reversed in the solid state.

Original languageEnglish (US)
Pages (from-to)580-586
Number of pages7
JournalJournal of the American Chemical Society
Volume132
Issue number2
DOIs
StatePublished - Jan 20 2010

ASJC Scopus subject areas

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

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