Poly(p-phenylene vinylene) derivatives with ester- and carboxy-functionalized substituents: a versatile platform towards polar functionalized conjugated polymers

I. Van Severen, F Motmans, L. Lutsen, TJ Cleij*, D. Vanderzande

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

15 Citations (Web of Science)

Abstract

A polar functionalized poly(p-phenylene vinylene) (ppv) derivative, ester containing poly(1,4-(2-(pentyloxy-5-carboxy methylester)-5-methoxyphenylene)vinylene), has been prepared via the sulfinyl precursor route. Subsequently, the carboxylic acid containing poly(1,4-(2-(5-carboxypentyloxy)-5-methoxyphenylene)vinylene) is readily obtained by the basic hydrolysis of the ester side groups. This carboxylic acid substituted polymer exhibits significantly improved optical properties as compared to previously reported similar polymers. To obtain polar functionalized ppv derivatives with more complex tailored substituents a versatile novel approach is presented based on the mitsunobu reaction conditions via a post-polymerization functionalization of the carboxylic acid side groups. Using these reaction conditions substituents containing various ester groups, i.e. 4-nitrobenzyl, 2-nitrobenzyl, 5-(methyl)furfural and 3-n,n-dimethylamino-1-propane, have been covalently attached to the phenylene ring. Analytical data of the functionalized polymers are consistent with a quantitative functional group substitution. The results demonstrate that the employed functionalization method allows for the introduction of a large variety of polar substituents in a straightforward manner.
Original languageEnglish
Pages (from-to)5466-5475
JournalPolymer
Volume46
Issue number15
DOIs
Publication statusPublished - 11 Jul 2005
Externally publishedYes

Keywords

  • polar functionalized PPV
  • sulfinyl precursor route
  • Mitsunobu reaction

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