Regioselectivity of the Pd-catalyzed synthesis of arylenevinylenes and its impact on polymer properties: Model reaction and polyreactions

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Klingelhöfer, Stephanie ; Schellenberg, Carsten ; Pommerehne, Jörn ; Bässler, Heinz ; Greiner, Andreas ; Heitz, Walter:
Regioselectivity of the Pd-catalyzed synthesis of arylenevinylenes and its impact on polymer properties: Model reaction and polyreactions.
In: Macromolecular Chemistry and Physics. Bd. 198 (1997) Heft 5 . - S. 1511-1530.
ISSN 1521-3935
DOI: https://doi.org/10.1002/macp.1997.021980516

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Abstract

The regioselectivity of Pd-catalyzed coupling reactions of functionalized benzenes and olefins with respect to the ratio of 1.2-product/1.1-product was monitored by model reactions. The coupling of halobenzenes, benzene triflate, and aryldiazonium salts was studied under various reaction conditions. In order to simulate corresponding polyreactions, special focus was on the coupling of ortho-substituted functionalized benzenes with ethylene or styrene in order to evaluate the input of mono- and disubstituted aryl monomers and the choice of the olefin on the regioselectivity of polyreactions. The results of the model reactions were transferred to the polyreactions. The polymers were characterized by NMR, absorption and photoluminescence spectroscopy as well as electroluminescence.