Novel derivatives of poly(4-hydroxystyrene) with easily removable tertiary, allylic, or benzylic ethers

Jean Frechet*, Nell Kallman, Boguslav Kryczka, Eva Eichler, Francis M. Houlihan, C. Grant Willson

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

The protection of poly(4-hydroxystyrene) and its 3,5-dimethyl analog through formation of its 2-cyclohexenyl, 1-phenyl-ethyl or t-butyl ether derivatives is easily accomplished. All of these ethers are selected as they contains structural features allowing for their facile elimination when deprotection is desired. In the case of the allylic and benzylic ethers,the monomers are easily prepared using a simple SN2 substitution reaction on p-hydroxybenzaldehyde or its 3,5-dimethyl analog followed by a Wittig methylenation. Chemical modification of poly(4-hydroxystyrene) using etherification procedures is also done easily but usually only affords partial functionalization; the remaining hydroxyl functional groups may however be blocked in-situ by addition of a second reagent. The active ether pendant groups of the polymers can be cleaved easily and quantitatively by thermolysis, acidolysis, or acid hydrolysis suggesting that the ether protected polymers may be useful as resist materials.

Original languageEnglish (US)
Pages (from-to)427-434
Number of pages8
JournalPolymer Bulletin
Volume20
Issue number5
DOIs
StatePublished - Nov 1 1988

ASJC Scopus subject areas

  • Chemistry(all)
  • Condensed Matter Physics
  • Polymers and Plastics
  • Materials Chemistry

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