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J Am Chem Soc. 2003 Dec 3;125(48):14708-9.

Comparison of "polynaphthalenes" prepared by two mechanistically distinct routes.

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  • 1Department of Chemistry and the Macromolecular Science and Engineering Program, The University of Michigan, Ann Arbor, MI 48109-1055, USA.


The Bergman cyclization has long been known to produce polymers as side products. More recently, this attribute has been harnessed for the production of conjugated materials. However, the structures of these polymers have not been established. To resolve this question, the metal-catalyzed polymerization of 1,4-dibromonaphthalene and thermal polymerization of o-diethynylbenzene were conducted. Two distinct polymers were obtained. Comparison of IR spectroscopy, MALDI-TOF MS, solid-state NMR spectroscopy, UV-vis reflectance spectroscopy, and pyrolysis GC-MS data indicates that only one of the polymers is consistent with poly(1,4-naphthalene).

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