Reversible radical ring-crossover polymerization of an alkoxyamine-containing dynamic covalent macrocycle

Go Yamaguchi, Yuji Higaki, Hideyuki Otsuka, Atsushi Takahara

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76 Citations (Scopus)


The synthesis of a macrocycle with alkoxyamine-based dynamic covalent bonds and its dynamic polymerization behavior are described. The macrocyclic alkoxyamine was synthesized by condensation of an alkoxyamine-based diol with adipoyl chloride under high-dilution conditions. Spectroscopic measurements revealed that one of the obtained macrocyclic compounds was a [2 + 2] adduct. The [2 + 2] macrocyclic compound acted as a monomer for "ring-crossover" polymerization to afford the corresponding polymer with Mn = 2000-18 000 due to the intermolecular radical crossover reaction. The polymerization behavior strongly depended on concentration, time, and temperature. Furthermore, under high-dilution conditions, the obtained poly(alkoxyamine) depolymerized to the monomer or oligomers mainly by the intramolecular radical exchange process.

Original languageEnglish
Pages (from-to)6316-6320
Number of pages5
Issue number15
Publication statusPublished - Jul 26 2005

All Science Journal Classification (ASJC) codes

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


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