145817-08-9Relevant academic research and scientific papers
Scope and Limitations of a New Highly Selective Synthesis of Unsymmetrical Monomers for the Synthesis of Precursors toward Poly(arylenevinylene)s
van der Borght, Michael,Vanderzande, Dirk,Adriaensens, Peter,Gelan, Jan
, p. 284 - 289 (2000)
In our laboratory a precursor route to poly(p-phenylenevinylene) derivatives is developed in which unsymmetrically substituted p-xylene derivatives, possessing a benzylic sulfinylalkyl group, are used as monomers. Because of this unsymmetry, we were forced to investigate thoroughly the synthesis of these sulfoxides, as we start from symmetric and readily accessible molecules, namely, bis(halomethyl)-p-xylene derivatives. In a former publication, a new extremely effective route for the production of these unsymmetrically substituted sulfinyl monomers was presented. This paper expands upon these previously reported results. To examine the scope and limitations of this elegant route, this new method was applied to the synthesis of various derivatives not included in the initial work.
Complete assignment of 1H and 13C NMR spectra of a set of sulphinyl and sulphonyl monomers toward poly(p-phenylenevinylene) precursors
Van Breemen, Albert J. J. M.,Adriaensens, Peter J.,Issaris, Anna C. J.,De Kok, Margreet M.,Vanderzande, Dirk J. M.,Gelan, Jan M. J. V.
, p. 129 - 134 (2007/10/03)
The complete assignment of the 1H and 13C NMR spectra of sulphinyl and sulphonyl monomers toward poly(p-phenylenevinylene) precursors is presented. For all compounds the same protocol could be used. Resonance assignments were achieve
Highly Selective Route for Producing Unsymmetrically Substituted Monomers toward Synthesis of Conjugated Polymers Derived from Poly(p-phenylene vinylene)
Van Breemen, Albert J. J. M.,Vanderzande, Dirk J. M.,Adriaensens, Peter J.,Gelan, Jan M. J. V.
, p. 3106 - 3112 (2007/10/03)
A new convenient route for producing unsymmetrically substituted sulfinyl monomers of precursor polymers toward poly(p-phenylene vinylene) is described. Upon treating a symmetrical bissulfonium salt with a thiolate anion, an unexpected high selectivity for the monosubstituted thioethers (90%) is obtained. Optimization of the reaction conditions showed that the stoichiometry of the reactants in this reaction is important to ensure the high selectivity and to prevent unwanted side reactions. Reaction of equimolar amounts of reagents at ambient temperature gave the best results. A mechanism consistent with these results, supported by UV-vis experiments, is presented. Selective oxidation of the thioethers yielded the sulfinyl monomers. By using this new route, it was possible to increase the overall yield by a factor of 2, as compared to the route previously used to obtain these compounds.
