Synthesis of aromatic oxazolyl‐ and carboxyl‐functionalized polymers: Atom transfer radical polymerization of styrene initiated by 2‐[(4‐bromomethyl)phenyl]‐4,5‐dihydro‐4,4‐dimethyloxazole |
| |
Authors: | Gabriel J. Summers Rejoice B. Maseko B. M. Parveen Beebeejaun Carol A. Summers |
| |
Affiliation: | 1. Department of Chemistry, University of South Africa, P.O. Box 392, UNISA, 0003, South Africa;2. St Marks High School, Department of Science, Mbabane, Swaziland;3. Department of Science, Mathematics and Technology Education, Faculty of Education, Groenkloof Campus, University of Pretoria, Pretoria 0002, South Africa |
| |
Abstract: | The synthesis of a new compound, 2‐[(4‐bromomethyl)phenyl]‐4,5‐dihydro‐4,4‐dimethyloxazole ( 1 ), and its utility in the synthesis of oxazoline‐functionalized polystyrene by atom transfer radical polymerization (ATRP) methods are described. Aromatic oxazolyl‐functionalized polymers were prepared by the ATRP of styrene, initiated by ( 1 ) in the presence of copper(I) bromide/2,2′‐bipyridyl catalyst system, to afford the corresponding α‐oxazolyl‐functionalized polystyrene ( 2 ). The polymerization proceeded via a controlled free radical polymerization process to produce the corresponding α‐oxazolyl‐functionalized polymers with predictable number‐average molecular weights, narrow molecular weight distributions in high‐initiator efficiency reactions. Post‐ATRP chain end modification of α‐oxazolyl‐functionalized polystyrene ( 2 ) to form the corresponding α‐carboxyl‐functionalized polystyrene ( 3 ) was achieved by successive acid‐catalyzed hydrolysis and saponification reactions. The polymerization processes were monitored by gas chromatography analyses. The unimolecular‐functionalized initiator and functionalized polymers were characterized by thin layer chromatography, spectroscopy, size exclusion chromatography, and nonaqueous titration analysis. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011. |
| |
Keywords: | atom transfer radical polymerization aromatic carboxylation 2‐[(4‐bromomethyl)phenyl]‐4,5‐dihydro‐4,4‐dimethyloxazole oxazolyl‐functionalized initiator oxazolyl‐functionalized polystyrene |
|
|