The cationic cyclopolymerization of o-vinylbenzaldehydes initiated by boron trifluoride is described. Unlike the incomplete conversion of o-vinylbenzaldehyde (1) at 0 C, α-methyl-substituted monomers (2) and (3) undergo cyclopolymerizations with complete conversions at -78 C. On the other hand, α-phenyl-substituted monomer (4) generated indenyl alcohol (7) when subjected to cationic polymerization conditions. The proposed mechanism for o-(α-methyl)vinylbenzaldehyde polymerization explains the importance of reaction temperature for polymer formation. Resulting amorphous poly(o-(α-methyl)vinylbenzaldehyde (10) exhibited good thermal stability (Tonset = 340 C) with a Tg of 153 C. Polymer (10) is a brittle and glassy plastic with a storage modulus (E′) of 3 × 108 Pa and elongation at break of ∼3%.

Original languageEnglish (US)
Pages (from-to)935-938
Number of pages4
JournalACS Macro Letters
Issue number10
StatePublished - Oct 15 2013

ASJC Scopus subject areas

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


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