Issue 83, 2016

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
20 Jul 2016
Accepted
10 Aug 2016
First published
25 Aug 2016

RSC Adv., 2016,6, 80328-80333

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

S. E. Bottle, J. Clement, M. Fleige, E. M. Simpson, Y. Guillaneuf, K. E. Fairfull-Smith, D. Gigmes and J. P. Blinco, RSC Adv., 2016, 6, 80328 DOI: 10.1039/C6RA18500B

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