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Selected Works of David W. Ball
Article
Synthesis of 1,3-Diphenyl-6-alkyl/aryl-Substituted Fulvene Chromophores: Observation of π–π Interactions in a 6-Pyrene-Substituted 1,3-Diphenylfulvene
Journal of Organic Chemistry
  • Andrew J. Peloquin, United States Air Force Academy
  • Rebecca L. Stone, United States Air Force Academy
  • Sarah E. Avila, United States Air Force Academy
  • Erlyn R. Rudico, United States Air Force Academy
  • Christopher B. Horn, United States Air Force Academy
  • Kim A. Gardner, United States Air Force Academy
  • David W. Ball, Cleveland State University
  • Jane E.B. Johnson, United States Air Force Academy
  • Scott T. Iacono, United States Air Force Academy
  • Gary J. Balaich, United States Air Force Academy
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Document Type
Article
Publication Date
1-1-2012
Disciplines
Abstract

The synthesis, structural, and electronic properties of nine 1,3-diphenyl-6-alkyl/aryl substituted pentafulvenes were studied. Pyrene ring π–π interactions were revealed from analysis of the experimental crystal packing of 1,3-diphenyl-6-(1-pyrene)fulvene and supporting DFT calculations. Photophysical properties derived from UV–vis and fluorescence emission measurements demonstrated tunable and low HOMO–LUMO band gaps for the series. The presented results point to a model synthetic approach for incorporation of extended π systems and donor-π-acceptor groups for fulvene-based electronic materials.

Comments

We acknowledge the Air Force Office of Scientific Research and the Department
of Chemistry, USAF Academy, for funding.

DOI
10.1021/jo301101x
Citation Information
Peloquin, A. J.; Stone, R. L.; Avila, S. E.; Rudico, E. R.; Horn, C. B.; Gardner, K. A.; Ball, D. W.; Johnson, J. E. B.; Iacono, S. T.; Balaich, G. J. Synthesis of 1,3-Diphenyl-6-alkyl/aryl-Substituted Fulvene Chromophores: Observation of π–π Interactions in a 6-Pyrene-Substituted 1,3-Diphenylfulvene. J. Org. Chem. 2012, 77, 6371-6376.