Light-active azaphenalene alkoxyamines: fast and efficient mediators of a photo-induced persistent radical effect

Bottle, Steven E., Clement, Jean-Louis, Fleige, Mirco, Simpson, Emily M., Guillaneuf, Yohann, Fairfull-Smith, Kathryn E., Gigmes, Didier, & Blinco, James P. (2016) Light-active azaphenalene alkoxyamines: fast and efficient mediators of a photo-induced persistent radical effect. RSC Advances, 6(83), pp. 80328-80333.

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Abstract

Here we report the first example of an alkoxyamine derived from an azaphenalene nitroxide, which when exposed to UV-light, readily undergoes homolysis to efficiently and cleanly re-form a nitroxide. This process selectively cleaves the C–O bond of the alkoxyamine and occurs orders of magnitude more rapidly than any other alkoxyamine homolysis previously described in the literature. We demonstrate the use of light to generate a persistent radical effect (PRE) and apply this to undertake radical insertion, radical exchange and proof of concept polymerization reactions.

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ID Code: 99917
Item Type: Journal Article
Refereed: Yes
DOI: 10.1039/C6RA18500B
ISSN: 2046-2069
Divisions: Current > QUT Faculties and Divisions > Science & Engineering Faculty
Copyright Owner: Copyright 2016 RSC Publishing
Deposited On: 12 Oct 2016 01:15
Last Modified: 13 Oct 2016 06:03

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