in Journal of Organic Chemistry, 78, pages 2040-2045, March 1, 2013.
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.
Co-Authors: Clelia W. Mallory, Colleen K. Regan, Rebecca J. Aspden, Annie Butler Ricks, Joy M. Racowski, Abigail I. Nash, Ahmara V. Gibbons, Patrick J. Carroll, and Joseph M. Bohen