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Mallory FB, Mallory CW, Regan CK, et al. Phenyl groups versus tert-butyl groups as solubilizing substituents for some [5]phenacenes and [7]phenacenes. J Org Chem. 2012;78(5):2040-5doi: 10.1021/jo3020819.
Mallory, F. B., Mallory, C. W., Regan, C. K., Aspden, R. J., Ricks, A. B., Racowski, J. M., Nash, A. I., Gibbons, A. V., Carroll, P. J., & Bohen, J. M. (2013). Phenyl groups versus tert-butyl groups as solubilizing substituents for some [5]phenacenes and [7]phenacenes. The Journal of organic chemistry, 78(5), 2040-5. https://doi.org/10.1021/jo3020819
Mallory, Frank B, et al. "Phenyl groups versus tert-butyl groups as solubilizing substituents for some [5]phenacenes and [7]phenacenes." The Journal of organic chemistry vol. 78,5 (2013): 2040-5. doi: https://doi.org/10.1021/jo3020819
Mallory FB, Mallory CW, Regan CK, Aspden RJ, Ricks AB, Racowski JM, Nash AI, Gibbons AV, Carroll PJ, Bohen JM. Phenyl groups versus tert-butyl groups as solubilizing substituents for some [5]phenacenes and [7]phenacenes. J Org Chem. 2013 Mar 01;78(5):2040-5. doi: 10.1021/jo3020819. Epub 2012 Dec 17. PMID: 23205719.
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J Org Chem. 2013 Mar 01;78(5):2040-5. doi: 10.1021/jo3020819. Epub 2012 Dec 17.

Phenyl groups versus tert-butyl groups as solubilizing substituents for some [5]phenacenes and [7]phenacenes.

The Journal of organic chemistry

Frank B Mallory, Clelia W Mallory, Colleen K Regan, Rebecca J Aspden, Annie Butler Ricks, Joy M Racowski, Abigail I Nash, Ahmara V Gibbons, Patrick J Carroll, Joseph M Bohen

Affiliations

  1. Department of Chemistry, Bryn Mawr College, Bryn Mawr, Pennsylvania 19010-2899, United States. [email protected]

PMID: 23205719 DOI: 10.1021/jo3020819

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.

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