Controlled functionalization of polystyrene: Introduction of reactive groups by multisite metalation with superbase and reaction with electrophiles

Lubomir Lochmann, Jean Frechet*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

28 Scopus citations

Abstract

The controlled functionalization of polystyrene using a process of metalation with a potassium superbase followed by reaction with electrophiles is described. The method is advantageous because metalation is extremely efficient, occurring rapidly even at room temperature, and the degree of functionalization can be controlled over a very broad range. Functionalization with trimethylsilyl groups allows effective monitoring and quantification of the metalation process. Other examples of modification include the introduction of small dendritic fragments by reaction with a dendron having an aldehydic focal point or the introduction of carboxylic acid pendant groups. This method, which has little effect on the polydispersity of the polymer, has broad applicability for the functionalization of a wide spectrum of polymers containing active hydrogens and may also be used to prepare randomly branched or star structures.

Original languageEnglish (US)
Pages (from-to)1767-1771
Number of pages5
JournalMacromolecules
Volume29
Issue number5
DOIs
StatePublished - Feb 26 1996

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

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