Ketone functionalized nitroxides: Synthesis, evaluation of N-alkoxyamine initiators, and derivatization of polymer termini

Greg O'Bryan, Aaron Nilsen, Rebecca Braslau

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Two ketone-bearing N-alkoxyamines have been prepared and evaluated as initiators in nitroxide-mediated polymerization. N-(1-Phenethyloxy)-5,5,8- trimethyl-7-phenyl-azanonan-2-one (1) forms polymers with excellent control of molecular weight and low polydispersities, whereas N-(l-phenethyloxy)-5,8- dimethyl-5,7-phenyl-azanonan-2-one (2) does not effect controlled polymerization at 125 °C. Polymers prepared from initiator 1 retain the ketone functionality on the nitroxide terminus. Near-quantitative functionalization is demonstrated via hydrazone formation.

Original languageEnglish (US)
Pages (from-to)7848-7854
Number of pages7
JournalMacromolecules
Volume40
Issue number22
DOIs
StatePublished - Oct 30 2007
Externally publishedYes

Fingerprint

Ketones
Polymers
Bearings (structural)
Polymerization
Hydrazones
Polydispersity
Molecular weight

ASJC Scopus subject areas

  • Materials Chemistry

Cite this

Ketone functionalized nitroxides : Synthesis, evaluation of N-alkoxyamine initiators, and derivatization of polymer termini. / O'Bryan, Greg; Nilsen, Aaron; Braslau, Rebecca.

In: Macromolecules, Vol. 40, No. 22, 30.10.2007, p. 7848-7854.

Research output: Contribution to journalArticle

@article{bcd8bad8a4e24a55b80b993bb273eb2d,
title = "Ketone functionalized nitroxides: Synthesis, evaluation of N-alkoxyamine initiators, and derivatization of polymer termini",
abstract = "Two ketone-bearing N-alkoxyamines have been prepared and evaluated as initiators in nitroxide-mediated polymerization. N-(1-Phenethyloxy)-5,5,8- trimethyl-7-phenyl-azanonan-2-one (1) forms polymers with excellent control of molecular weight and low polydispersities, whereas N-(l-phenethyloxy)-5,8- dimethyl-5,7-phenyl-azanonan-2-one (2) does not effect controlled polymerization at 125 °C. Polymers prepared from initiator 1 retain the ketone functionality on the nitroxide terminus. Near-quantitative functionalization is demonstrated via hydrazone formation.",
author = "Greg O'Bryan and Aaron Nilsen and Rebecca Braslau",
year = "2007",
month = "10",
day = "30",
doi = "10.1021/ma071039s",
language = "English (US)",
volume = "40",
pages = "7848--7854",
journal = "Macromolecules",
issn = "0024-9297",
publisher = "American Chemical Society",
number = "22",

}

TY - JOUR

T1 - Ketone functionalized nitroxides

T2 - Synthesis, evaluation of N-alkoxyamine initiators, and derivatization of polymer termini

AU - O'Bryan, Greg

AU - Nilsen, Aaron

AU - Braslau, Rebecca

PY - 2007/10/30

Y1 - 2007/10/30

N2 - Two ketone-bearing N-alkoxyamines have been prepared and evaluated as initiators in nitroxide-mediated polymerization. N-(1-Phenethyloxy)-5,5,8- trimethyl-7-phenyl-azanonan-2-one (1) forms polymers with excellent control of molecular weight and low polydispersities, whereas N-(l-phenethyloxy)-5,8- dimethyl-5,7-phenyl-azanonan-2-one (2) does not effect controlled polymerization at 125 °C. Polymers prepared from initiator 1 retain the ketone functionality on the nitroxide terminus. Near-quantitative functionalization is demonstrated via hydrazone formation.

AB - Two ketone-bearing N-alkoxyamines have been prepared and evaluated as initiators in nitroxide-mediated polymerization. N-(1-Phenethyloxy)-5,5,8- trimethyl-7-phenyl-azanonan-2-one (1) forms polymers with excellent control of molecular weight and low polydispersities, whereas N-(l-phenethyloxy)-5,8- dimethyl-5,7-phenyl-azanonan-2-one (2) does not effect controlled polymerization at 125 °C. Polymers prepared from initiator 1 retain the ketone functionality on the nitroxide terminus. Near-quantitative functionalization is demonstrated via hydrazone formation.

UR - http://www.scopus.com/inward/record.url?scp=36048953375&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=36048953375&partnerID=8YFLogxK

U2 - 10.1021/ma071039s

DO - 10.1021/ma071039s

M3 - Article

AN - SCOPUS:36048953375

VL - 40

SP - 7848

EP - 7854

JO - Macromolecules

JF - Macromolecules

SN - 0024-9297

IS - 22

ER -