Frank Mallory, Chemistry, “Phenyl Groups versus tert-Butyl Groups as Solubilizing Substituents for Some [5]Phenacenes and [7]Phenacenes,”

Posted September 12th, 2013 at 11:41 am.

The Journal of Organic Chemistry, March 2013.

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.

Filed under: chemistry,sciences Tags: , by Diana Campeggio

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