A Profluorescent Azaphenalene Nitroxide for Nitroxide‐Mediated Polymerization1
John M. Colwell A , James P. Blinco A , Courtney Hulbert A , Kathryn E. Fairfull‐Smith A and Steven E. Bottle A B
+ Author Affiliations
- Author Affiliations
A ARC Centre of Excellence for Free Radical Chemistry and Biotechnology,Queensland University of Technology, GPO Box 2434, Brisbane,Queensland, Australia.
B Corresponding author. Email: s.bottle@qut.edu.au
Australian Journal of Chemistry 64(4) 426-432 https://doi.org/10.1071/CH10404
Submitted: 5 November 2010 Accepted: 1 February 2011 Published: 18 April 2011
Abstract
A novel nitroxide‐mediated polymerization (NMP) control agent; 1,1,3,3‐tetramethyl‐2,3‐dihydro‐2‐azaphenalen‐2‐yloxyl (TMAO), was used in the free‐radical polymerization of styrene. The conversion of styrene during NMP was studied using FT‐Raman spectroscopy and the effectiveness of TMAO as a NMP control agent was assessed by GPC analysis. Fidelity of the TMAO‐alkoxyamine end‐group on the synthesized polymers was confirmed by GPC, UV‐Vis and fluorescence spectroscopic analyses. Comparison to the well known NMP control agent, TEMPO was made. TMAO showed control of molecular weight approaching that of TEMPO. Attempts to improve the properties of TMAO as an NMP control agent by synthesizing an analogue with bulkier substituents around the nitroxide did not generate the target molecule but demonstrated some of the interesting chemistry of the azaphenalene ring system.
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