177752-90-8Relevant academic research and scientific papers
Identification and quantification of polymerization defects in 13C-labeled sulfinyl and gilch OC1C10-PPV by NMR spectroscopy
Roex,Adriaensens,Vanderzande,Gelan
, p. 5613 - 5622 (2007/10/03)
By using selectively 13C-labeled sulfinyl and Gilch polymers, only noneliminated groups were demonstrated to be present in significant amounts (ca. 6.9%) in the sulfinyl conjugated OC1C10PPV. By means of a two-step elimination procedure, this amount could be reduced to a level less than 0.5%. In the Gilch route on the other hand, a tolane-bisbenzyl unit was confirmed to be the main structural defect. Furthermore, noneliminated groups were clearly present. For both polymerization routes no indications for other types of defects such as cross-links or branching, were detected while strong indications for carbonyl type end groups were found. The nature of all "defects" was elucidated by applying liquid 1D and 2D NMR spectroscopy and the amount was calculated based on fully quantitative 13C NMR spectra.
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 (2007/10/03)
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.
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.
