A series of 1,3-diphenyl-6-alkyl/arylfulvenes was prepared, and the electrochemical properties were investigated. The addition of phenyl groups about the fulvene raised the reduction potential and helped to stabilize the electrochemically generated radical anion. The addition of various functional groups onto the phenyl ring at the 6-position of 1,3,6-triphenylfulvene results in a linear free energy relationship between reduction potential and the Hammett substituent constant, σ. Further extending the conjugation at the 6-position of 1,3-diphenyl-6-arylfulvenes increases the reversibility of the redox reactions, but does not appear to further stabilize the generated radical anion. This in-depth investigation provides evidence that the compounds studied may have utility in light-harvesting applications.
Article
Synthesis, Electrochemical Characterization, and Linear Free Energy Relationship of 1,3-Diphenyl-6-alkyl/arylfulvenes
Journal of Organic Chemistry
Document Type
Article
Publication Date
10-21-2016
Disciplines
Abstract
DOI
10.1021/acs.joc.6b01698
Citation Information
Godman, N. P.; Adas, S. K.; Hellwig, K. M.; Ball, D. W.; Balaich, G. J.; Iacono, S. T. Synthesis, Electrochemical Characterization, and Linear Free Energy Relationship of 1,3-Dipheny1-6-alkyl/arylfulvenes. J. Org. Chem. 2016, 81, 9630-9638.
This work was supported by the Air Force Office of Scientific Research (AFOSR) and the Defense Threat Reduction Agency (DTRA) − Joint Science and Technology Office for Chemical and Biological Defense (MIPR no. HDTRA13964). N.P.G. and S.K.A. were supported through the National Research Council (NRC) Postdoctoral Research Associateship Program.