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

• Main Authors: Yeniad, B Bahar, Koklukaya, O, Naik, H Hemantkumar, Fijten, MWM Martin, Koning, CE Cor, Heise, A Andreas
• Format: Article in Journal/Newspaper
• Language: English
• Published: 2013
• Subjects: Antarc*; Antarctica
• Online Access: http://repository.tue.nl/750802

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