Chiroptical Properties of Homopolymers and Block Copolymers Synthesized from the Enantiomeric Monomers N-Acryloyl-l-Alanine and N-Acryloyl-d-Alanine Using Aqueous RAFT Polymerization*

Brad S. Lokitz; Jonathan E. Stempka; Adam W. York; Yuting Li; Hitesh K. Goel; G. Reid Bishop; Charles L. McCormick

doi:10.1071/CH06264

RESEARCH FRONT

Chiroptical Properties of Homopolymers and Block Copolymers Synthesized from the Enantiomeric Monomers N-Acryloyl-l-Alanine and N-Acryloyl-d-Alanine Using Aqueous RAFT Polymerization*

Brad S. Lokitz ^A , Jonathan E. Stempka ^A , Adam W. York ^A , Yuting Li ^A , Hitesh K. Goel ^B , G. Reid Bishop ^B and Charles L. McCormick ^A ^C ^D

+ Author Affiliations

- Author Affiliations

^A Department of Polymer Science, University of Southern Mississippi, Hattiesburg, MS 39406, USA.

^B Department of Chemistry and Biochemistry, Mississippi College, Clinton, MS 39058, USA.

^C Department of Chemistry and Biochemistry, University of Southern Mississippi, Hattiesburg, MS 39406, USA.

^D Corresponding author. Email: charles.mccormick@usm.edu

Australian Journal of Chemistry 59(10) 749-754 https://doi.org/10.1071/CH06264
Submitted: 26 July 2006 Accepted: 26 September 2006 Published: 30 October 2006

Abstract

Chiral homo- and block copolymers based on the enantiomeric monomers N-acryloyl-l-alanine (ALAL) and N-acryloyl-d-alanine (ADAL) were prepared directly in water using controlled reversible addition–fragmentation chain transfer (RAFT) polymerization. The polymerization of the chiral monomers proceeded in a controlled fashion producing the respective homopolymers, block copolymers, and a statistical copolymer with targeted molecular weights and narrow molecular weight distributions. The chiroptical activity of these biomimetic polymers and their analogous model compounds was investigated using circular dichroism (CD). P(ALAL) and P(ADAL) were shown to be optically active exhibiting mirror image CD spectra. In addition, statistical and enantiomeric block copolymers prepared at 1:1 stochiometric ratios exhibited virtually no optical activity.

Acknowledgements

We gratefully acknowledge The Department of Energy (DE-FC26-01BC15317), Genzyme, MRSEC program of the National Science Foundation (DR-0213883), and the Robert M. Hearin Foundation as well as Mississippi College and the W. M. Keck Foundation for financial support. We would also like to thank Wako Chemicals for donating V-501.

References

^* Paper number 126 in a series on Water Soluble Polymers.

Chiroptical Properties of Homopolymers and Block Copolymers Synthesized from the Enantiomeric Monomers N-Acryloyl-l-Alanine and N-Acryloyl-d-Alanine Using Aqueous RAFT Polymerization*

Abstract

Acknowledgements

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