The methylation rate for a series of pyridine-containing phenylene ethynylene oligomers shows a nonlinear dependence on chain length, with a significant rate enhancement observed for oligomers that adopt a folded, helical conformation. The folded structure provides a microenvironment that lowers the energy barrier for the methylation reaction. Of these noncovalent interactions, the largest stabilization may arise from binding of methyl iodide in the hydrophobic cavity of the folded oligomer, in close proximity to the pyridine nucleophile.

Original languageEnglish (US)
Pages (from-to)1648-1649
Number of pages2
JournalJournal of the American Chemical Society
Issue number6
StatePublished - Feb 18 2004

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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