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

Go Yamaguchi, Yuji Higaki, Hideyuki Otsuka, Atsushi Takahara

Research output: Contribution to journalArticle

65 Citations (Scopus)

Abstract

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
JournalMacromolecules
Volume38
Issue number15
DOIs
Publication statusPublished - Jul 26 2005

Fingerprint

Macrocyclic Compounds
Polymerization
Dilution
Monomers
Covalent bonds
Oligomers
Condensation
Polymers
Temperature

All Science Journal Classification (ASJC) codes

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

Cite this

Reversible radical ring-crossover polymerization of an alkoxyamine-containing dynamic covalent macrocycle. / Yamaguchi, Go; Higaki, Yuji; Otsuka, Hideyuki; Takahara, Atsushi.

In: Macromolecules, Vol. 38, No. 15, 26.07.2005, p. 6316-6320.

Research output: Contribution to journalArticle

Yamaguchi, Go ; Higaki, Yuji ; Otsuka, Hideyuki ; Takahara, Atsushi. / Reversible radical ring-crossover polymerization of an alkoxyamine-containing dynamic covalent macrocycle. In: Macromolecules. 2005 ; Vol. 38, No. 15. pp. 6316-6320.
@article{06f4faea217343a7a50b56019ac05ded,
title = "Reversible radical ring-crossover polymerization of an alkoxyamine-containing dynamic covalent macrocycle",
abstract = "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.",
author = "Go Yamaguchi and Yuji Higaki and Hideyuki Otsuka and Atsushi Takahara",
year = "2005",
month = "7",
day = "26",
doi = "10.1021/ma0503209",
language = "English",
volume = "38",
pages = "6316--6320",
journal = "Macromolecules",
issn = "0024-9297",
publisher = "American Chemical Society",
number = "15",

}

TY - JOUR

T1 - Reversible radical ring-crossover polymerization of an alkoxyamine-containing dynamic covalent macrocycle

AU - Yamaguchi, Go

AU - Higaki, Yuji

AU - Otsuka, Hideyuki

AU - Takahara, Atsushi

PY - 2005/7/26

Y1 - 2005/7/26

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=23744478889&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=23744478889&partnerID=8YFLogxK

U2 - 10.1021/ma0503209

DO - 10.1021/ma0503209

M3 - Article

AN - SCOPUS:23744478889

VL - 38

SP - 6316

EP - 6320

JO - Macromolecules

JF - Macromolecules

SN - 0024-9297

IS - 15

ER -