Please use this identifier to cite or link to this item: http://hdl.handle.net/1942/4978
Title: Highly selective route for producing unsymmetrically substituted monomers towards synthesis of conjugated polymers derived from poly(p-phenylene vinylene)
Authors: VAN BREEMEN, Albert
VANDERZANDE, Dirk 
ADRIAENSENS, Peter 
GELAN, Jan 
Issue Date: 1999
Publisher: AMER CHEMICAL SOC
Source: Journal of organic chemistry, 64. p. 3106-3112
Abstract: 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.
Keywords: SOLUBLE PRECURSOR METHOD; ALPHA,ALPHA'-BIS(TETRAHYDROTHIOPHENIO)-P-XYLENE DICHLORIDE; POLYMERIZATION; MECHANISM; DERIVATIVES; SULFOXIDES; OXIDATION; LIGHT
Document URI: http://hdl.handle.net/1942/4978
DOI: 10.1021/jo9821022
ISI #: 000080171200029
Type: Journal Contribution
Validations: ecoom 2000
Appears in Collections:Research publications

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