title: Phenyl groups versus tert-butyl groups as solubilizing substituents for some [5]phenacenes and [7]phenacenes.
abstract: In recent years, we have used the photocyclizations of diarylethylenes to synthesize a number of [n]phenacenes in the hope that they might be useful as the bridging groups for electron transfer processes in donor-bridge-acceptor molecules. Because [n]phenacenes with n > 5 are very insoluble, their synthesis and characterization has required the attachment of solubilizing substituents such as tert-butyl. The studies of Pascal and co-workers of some large polynuclear aromatic compounds having multiple phenyl substituents prompted us to explore the use of phenyls as alternative solubilizing groups for [n]phenacenes. Although phenyl groups turned out to provide significantly less solubilization than tert-butyl groups in these compounds, we found some interesting structural comparisons of the phenyl-substituted and tert-butyl-substituted [n]phenacenes.
authors.affiliation: Department of Chemistry, Bryn Mawr College, Bryn Mawr, Pennsylvania 19010-2899, United States. fmallory@brynmawr.edu
authors.forename: Frank B
authors.initials: FB
authors.lastname: Mallory
authors.forename: Clelia W
authors.initials: CW
authors.lastname: Mallory
authors.forename: Colleen K
authors.initials: CK
authors.lastname: Regan
authors.forename: Rebecca J
authors.initials: RJ
authors.lastname: Aspden
authors.forename: Annie Butler
authors.initials: AB
authors.lastname: Ricks
authors.forename: Joy M
authors.initials: JM
authors.lastname: Racowski
authors.forename: Abigail I
authors.initials: AI
authors.lastname: Nash
authors.forename: Ahmara V
authors.initials: AV
authors.lastname: Gibbons
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Carroll
authors.forename: Joseph M
authors.initials: JM
authors.lastname: Bohen