Are o-Nitrobenzyl (Meth)acrylate Monomers Polymerizable by Controlled-Radical Polymerization?

Schumers, Jean-Marc; Fustin, Charles-Andre; Can, Aydın; Hoogenboom, Richard; Schubert, Ulrich S.; Gohy, Jean-Francois

Abstract:

We report on the controlled-radical polymerization of the photocleavable o-nitrobenzyl methacrylate (NBMA) and o-nitrobenzyl acrylate (NBA) monomers. Atom transfer radical polymerization (ATRP), reversible addition-fragmentation chain transfer polymerization (RAFT), and nitroxide-mediated polymerization (NMP) have been evaluated. For all methods used, the acrylate-type monomer does not polymerize, or polymerizes very slowly in a noncontrolled manner. The methacrylate-type monomer can be polymerized by RAFT with some degree of control (PDI ~ 1.5) but leading to molar masses up to 11,000 g/mol only. ATRP proved to be the best method since a controlled-polymerization was achieved when conversions are limited to 30%. In this case, polymers with molar masses up to 17,000 g/mol and polydispersity index as low as 1.13 have been obtained. VVC

Year:

2009

Type of Publication:

Article

Journal:

Journal of Polymer Science: Part A: Polymer Chemistry

Volume:

47

Pages:

6504 - 6513