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

Greg O'Bryan; Aaron Nilsen; Rebecca Braslau

doi:10.1021/ma071039s

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

Greg O'Bryan, Aaron Nilsen, Rebecca Braslau

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12 Scopus citations

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 language	English (US)
Pages (from-to)	7848-7854
Number of pages	7
Journal	Macromolecules
Volume	40
Issue number	22
DOIs	https://doi.org/10.1021/ma071039s
State	Published - Oct 30 2007
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Inorganic Chemistry
Materials Chemistry

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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",

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doi = "10.1021/ma071039s",

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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.

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

Abstract

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