ORGN 530 |
Novel polyphenylene structures related to "cubic graphite"
| Xianfeng Shen, Douglas M. Ho, and Robert A. Pascal Jr. Department of Chemistry, Princeton University, Frick Laboratory, Washington Road, Princeton, NJ 08544 |
Abstract: Two substructures (1 and 2 ) of “phenylogous cubic graphite” were prepared in very short syntheses. The palladium-catalyzed Suzuki coupling reaction between 1,2-bis(4-bromophenyl)-3,4,5,6-tetraphenylbenzene and the corresponding hexaphenylbenzene bis(boronic acid) gave a mixture of linear and cyclic oligomers of hexaphenylbenzene containing two to six hexaphenylbenzene subunits. An X-ray crystal structure of the tetrameric oligomer showed it to be the substructure 1 (C168H112). A four-step convergent synthesis gave the dendrimeric substructure 2 (C294H198) in an overall yield of 41% via palladium-catalyzed coupling and Diels-Alder reactions. |
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Heterocycles, Aromatics, Metal-Mediated Reactions, Physical Organic, Materials
9:00 AM-11:00 AM, Wednesday, March 26, 2003 Convention Center -- Hall I-1, Poster
Sci-Mix
8:00 PM-10:00 PM, Monday, March 24, 2003 Convention Center -- Hall G, Sci-Mix
Division of Organic Chemistry
The 225th ACS National Meeting, New Orleans, LA, March 23-27, 2003
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