Synthesis of enantiopure homo and copolymers by raft polymerization and investigation of their enantioselective lipase‐catalyzed esterification

• Published in: Journal of Polymer Science Part A: Polymer Chemistry
• Main Authors: Yeniad, Bahar, Köklükaya, N. Oruç, Naik, Hemantkumar, Fijten, M. W. Martin, Koning, Cor E., Heise, Andreas
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 2012
• Subjects: Antarc*; Antarctica
• Online Access: http://dx.doi.org/10.1002/pola.26272; https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fpola.26272; https://onlinelibrary.wiley.com/doi/pdf/10.1002/pola.26272

Abstract Homo and copolymers were synthesized from enantionpure ( R )‐ and ( S )‐1‐(4‐vinylphenyl)ethanol by reversible addition‐fragmentation chain transfer polymerization. The polymerization conditions were optimized resulting in dioxane as the preferred reaction solvent. First‐order polymerization kinetics and well‐defined enantiopure homopolymers with low dispersities were obtained. In agreement with their enantiomeric composition, the ( R ) and ( S ) ‐ polymers gave opposite optical rotation of light. Polymer analogous esterification of the chiral hydroxy groups catalyzed by enantioselective Candida antarctica Lipase B was strongly ( R )‐selective. Esterification on the homopolymer and copolymers could be achieved to a maximum of around 50 %. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013