Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH FRONT (Open Access)

On the Origins of Nitroxide Mediated Polymerization (NMP) and Reversible Addition–Fragmentation Chain Transfer (RAFT)*

Ezio Rizzardo A C and David H. Solomon B C

A CSIRO Materials Science and Engineering, Clayton South, Melbourne, Vic. 3169, Australia.

B Department of Chemical & Biomolecular Engineering, The University of Melbourne, Parkville, Melbourne, Vic. 3010, Australia.

C Corresponding authors. Email: ezio.rizzardo@csiro.au; davids@unimelb.edu.au




Ezio Rizzardo (right) graduated with first class honours in applied organic chemistry from the University of New South Wales and was awarded a Ph.D. in organic chemistry by the University of Sydney in 1969 for his studies on the photochemistry of organic nitro compounds. He joined David Solomon’s group at CSIRO in 1976 after postdoctoral work on the synthesis of biologically active compounds with Richard Turner at Rice University (Houston), Sir Derek Barton at RIMAC (Boston), and Arthur Birch at the ANU (Canberra). His research at CSIRO has focused on the development of methods for understanding and controlling polymerization processes. He is the co-author of some 200 journal papers, which to date have received over 13000 citations, and co-inventor on 44 worldwide patents. He is a Fellow of the Royal Society of London, the Australian Academy of Science and the Australian Academy of Technological Sciences and Engineering, and the recipient of the Australian Polymer Medal, the CSIRO Chairman’s Gold Medal and the Australian Government’s Centenary Medal for contributions to society and polymer science. David Solomon (left) graduated from the University of New South Wales with a Ph.D. in 1959 and a D.Sc. in 1968; he also holds a Diploma in Chemistry from Sydney Technical College (1950). During his studies, he worked for Dulux and this is where his interest in the chemistry of radical polymerization began. He was seconded to work at ICI Paints Division in 1959 and returned to Dulux to set up their polymer research group. In 1963, he joined CSIRO and set up the polymer research section. He recruited Ezio into this group and together they developed techniques to better understand radical chemistry and eventually living radical systems. David was also the principal inventor of the world’s first polymer banknote. He was President of the Royal Australian Chemical Institute (RACI) from 1979 to 1980. He is a Fellow of the Royal Society of London, the Australian Academy of Science, the Australian Academy of Technological Sciences and Engineering (Foundation Fellow), the RACI and the Institute of Chemical Engineers. He has received numerous awards, including Member of the Order of Australia, D.App.Sc. (Honoris Causa) (University of Melbourne), and is the sole recipient of Australia’s Bicentennial Science Achievement Award. The Polymer Division of the RACI has recognized Dave’s contributions to polymer science with the annual Solomon Lecture given by a prestigious polymer scientist.

Australian Journal of Chemistry 65(8) 945-969 http://dx.doi.org/10.1071/CH12194
Submitted: 13 April 2012  Accepted: 17 May 2012   Published: 5 July 2012

Abstract

The early experiments on radical polymerization, which were to lead to a study of nitroxide trapping of the initiation step and the interest in defect groups, particularly the macromonomers formed by termination by disproportionation, are discussed. Results from the nitroxide trapping clearly show that the initiation step ranges from simple clean addition to the head of the monomer, to complex addition/abstraction reactions. Careful selection of the monomer/initiation system is emphasized with particular reference to two common monomers, styrene and methyl methacrylate, and two initiating radicals, t-butoxy and benzoyloxy. The discovery of nitroxide mediated polymerization (NMP) from observations made during the nitroxide trapping work is reported and the ability to have a living radical system demonstrated with numerous examples. Similarly, the study of the copolymerization of macromonomers, formed by disproportionation of the propagating chains, is discussed with the discovery of β-scission and an early form of addition–fragmentation reported. The evolution of reversible addition–fragmentation chain transfer (RAFT) to a highly versatile and commercially attractive radical system is reported and the detailed chemistry behind the discovery of this living radical system discussed. Both NMP and RAFT enable the synthesis of structures not previously possible by radical polymerization and in some cases not possible by any other process.


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