Synthesis, Electrochemical Characterization, and Linear Free Energy Relationship of 1,3-Diphenyl-6-alkyl/arylfulvenes
Journal of Organic Chemistry
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.
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.