Synthesis, Electrochemical Characterization, and Linear Free Energy Relationship of 1,3-Diphenyl-6-alkyl/arylfulvenes.
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.
Department of Chemistry and Chemistry Research Center, United States Air Force Academy , Colorado Springs, Colorado 80840, United States.
Nicholas P
NP
Godman
Department of Chemistry and Chemistry Research Center, United States Air Force Academy , Colorado Springs, Colorado 80840, United States.
Sonya K
SK
Adas
Department of Chemistry and Chemistry Research Center, United States Air Force Academy , Colorado Springs, Colorado 80840, United States.
Karl M
KM
Hellwig
Department of Chemistry, Cleveland State University , Cleveland, Ohio 44415, United States.
David W
DW
Ball
Department of Chemistry and Chemistry Research Center, United States Air Force Academy , Colorado Springs, Colorado 80840, United States.
Gary J
GJ
Balaich
Department of Chemistry and Chemistry Research Center, United States Air Force Academy , Colorado Springs, Colorado 80840, United States.
Scott T
ST
Iacono